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161596-47-0

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161596-47-0 Usage

Chemical Properties

White powder

Uses

N-(S)-Glycidylphthalimide is a phthalimide derivative used as an intermediate in the preparation of the antibiotic Linezolid (L466500).

Check Digit Verification of cas no

The CAS Registry Mumber 161596-47-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,1,5,9 and 6 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 161596-47:
(8*1)+(7*6)+(6*1)+(5*5)+(4*9)+(3*6)+(2*4)+(1*7)=150
150 % 10 = 0
So 161596-47-0 is a valid CAS Registry Number.
InChI:InChI=1/C11H9NO3/c13-10-8-3-1-2-4-9(8)11(14)12(10)5-7-6-15-7/h1-4,7H,5-6H2/t7-/m0/s1

161596-47-0 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • TCI America

  • (G0328)  (S)-N-Glycidylphthalimide  >98.0%(GC)

  • 161596-47-0

  • 5g

  • 690.00CNY

  • Detail
  • TCI America

  • (G0328)  (S)-N-Glycidylphthalimide  >98.0%(GC)

  • 161596-47-0

  • 25g

  • 2,450.00CNY

  • Detail
  • Aldrich

  • (671606)  (S)-(+)-N-(2,3-Epoxypropyl)phthalimide  ≥99.0% (GC)

  • 161596-47-0

  • 671606-1G

  • 285.48CNY

  • Detail
  • Aldrich

  • (671606)  (S)-(+)-N-(2,3-Epoxypropyl)phthalimide  ≥99.0% (GC)

  • 161596-47-0

  • 671606-5G

  • 1,068.21CNY

  • Detail

161596-47-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name (S)-(+)-GLYCIDYL PHTHALIMIDE

1.2 Other means of identification

Product number -
Other names (S)-(+)-N-(2,3-Epoxypropyl)phthalimide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:161596-47-0 SDS

161596-47-0Synthetic route

2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione
148857-42-5

2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With sodium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Reflux; Green chemistry;94%
With sodium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Reflux;89%
With potassium phosphate In 1,2-dichloro-ethane at 80℃; for 14h; Product distribution / selectivity;n/a
1H-isoindole-1,3(2H)-dione, 2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]
40137-25-5

1H-isoindole-1,3(2H)-dione, 2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
Stage #1: 1H-isoindole-1,3(2H)-dione, 2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl] With hydrogen bromide In 1,2-dichloro-ethane at 10 - 15℃; for 4h;
Stage #2: With sodium methylate In methanol at 0 - 15℃; for 3h;
93.6%
Multi-step reaction with 4 steps
1: hydrogenchloride / water / 2 h / 60 - 67 °C / Industrial scale
2: pyridinium p-toluenesulfonate / toluene / 0.25 h / 30 - 50 °C / Industrial scale
3: chloro-trimethyl-silane / toluene / 2.5 h / 30 °C
4: sodium methylate / methanol / 20 h / 30 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride / water / 2 h / 60 - 67 °C / Industrial scale
2: pyridinium p-toluenesulfonate / toluene / 3 h / Dean-Stark; Reflux; Industrial scale
3: N-Bromosuccinimide / 1,2-dichloro-ethane / 1.33 h / 12 - 22 °C / Industrial scale
4: sodium methylate / toluene; methanol / 5.17 h / 9 - 22 °C / Industrial scale
View Scheme
phthalimide
136918-14-4

phthalimide

(S)-oxiranemethanol
60456-23-7

(S)-oxiranemethanol

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;91%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;91%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20 - 25℃; for 18h;80%
phthalimide
136918-14-4

phthalimide

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With benzyltrimethylammonium chloride In isopropyl alcohol at 40℃; for 22h;90%
With potassium tert-butylate; benzyltrimethylammonium chloride; sodium carbonate In tetrahydrofuran at 50℃; for 39h;81%
With benzyltrimethylammonium chloride; sodium hydrogencarbonate In isopropyl alcohol at 20℃; for 25h;80%
C15H17NO4

C15H17NO4

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
Stage #1: C15H17NO4 With hydrogenchloride In dichloromethane; water at 10 - 15℃; for 4h;
Stage #2: With sodium methylate In methanol at 0 - 15℃; for 3h; Reagent/catalyst;
89.7%
C17H21NO4

C17H21NO4

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
Stage #1: C17H21NO4 With hydrogen iodide In chloroform at 10 - 15℃; for 4h;
Stage #2: With sodium ethanolate In ethanol at 0 - 15℃; for 3h;
85.9%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

potassium phtalimide
1074-82-4

potassium phtalimide

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With benzyltrimethylammonium chloride In isopropyl alcohol at 10℃; for 46h;83%
With benzyltrimethylammonium chloride In tetrahydrofuran at 50℃; for 44h;74%
With benzyltrimethylammonium chloride In methanol at 20℃; for 15h;68%
phthalimide
136918-14-4

phthalimide

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

A

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

B

2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione
148857-42-5

2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With potassium fluoride on basic alumina In 2-methyltetrahydrofuran for 3h; Inert atmosphere; Reflux; stereospecific reaction;A 10%
B 83%
(S)-epichlorohydrin
67843-74-7

(S)-epichlorohydrin

potassium phtalimide
1074-82-4

potassium phtalimide

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
at 70℃; for 1h; Temperature;83%
With N-benzyl-N,N,N-triethylammonium chloride; potassium iodide In isopropyl alcohol at 28℃; for 72h; Reagent/catalyst; Temperature; Solvent;88.1 g
1H-isoindole-1,3(2H)-dione, 2-[2-(benzoyloxy)-3-bromopropyl]

1H-isoindole-1,3(2H)-dione, 2-[2-(benzoyloxy)-3-bromopropyl]

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With sodium methylate In methanol; toluene at 9 - 22℃; for 5.16667h; Industrial scale;80.8%
phthalimide
136918-14-4

phthalimide

(S)-epichlorohydrin
67843-74-7

(S)-epichlorohydrin

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
Stage #1: phthalimide; (S)-epichlorohydrin With methylamine In isopropyl alcohol at 60℃; for 5h;
Stage #2: With sodium methylate In methanol; isopropyl alcohol at 10 - 30℃; Solvent; Reagent/catalyst;
77.5%
Stage #1: phthalimide; (S)-epichlorohydrin With N-benzyl-N,N,N-triethylammonium chloride; sodium carbonate In isopropyl alcohol at 20 - 40℃;
Stage #2: With potassium tert-butylate In isopropyl alcohol at 5 - 10℃;
With sodium acetate In isopropyl alcohol at 65 - 70℃;5 g
With 1-hexylamine hydrochloride; potassium tert-butylate; potassium iodide In isopropyl alcohol at 28℃; for 72h;84.5 g
phthalimide
136918-14-4

phthalimide

(R)-oxiranemethanol
57044-25-4

(R)-oxiranemethanol

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 4h;53%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

potassium phtalimide
1074-82-4

potassium phtalimide

A

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
181140-34-1

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione

B

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With benzyltrimethylammonium chloride In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;
2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione
19667-37-9, 34839-11-7, 148857-42-5, 148857-44-7

2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With potassium carbonate In toluene Reflux;n/a
In tetrahydrofuran; water
(S)-2-(2-acetoxy-3-bromo-propyl)-isoindole-1,3-dione
879507-96-7

(S)-2-(2-acetoxy-3-bromo-propyl)-isoindole-1,3-dione

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With potassium carbonate In methanol at 0℃; for 1h;
phthalimide
136918-14-4

phthalimide

(R)-glycidyl tosylate
113826-06-5

(R)-glycidyl tosylate

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In acetone at 35 - 60℃; for 12h;
With tetrabutylammomium bromide; potassium carbonate In acetone at 25 - 60℃; for 12h;
phthalimide
136918-14-4

phthalimide

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: aluminum oxide / 1-methyl-pyrrolidin-2-one / 64 - 68 °C
1.2: 0.5 h
2.1: potassium carbonate / toluene / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: aluminum oxide / 1-methyl-pyrrolidin-2-one / 64 - 68 °C
1.2: 0.5 h
2.1: potassium carbonate / toluene / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: aluminum oxide / 1-methyl-pyrrolidin-2-one / 64 - 68 °C
1.2: 0.5 h
2.1: potassium carbonate / toluene / Reflux
View Scheme
phthalimide
136918-14-4

phthalimide

(S)-epichlorohydrin
67843-74-7

(S)-epichlorohydrin

A

2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione
19667-37-9, 34839-11-7, 148857-42-5, 148857-44-7

2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione

B

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With aluminum oxide In 1-methyl-pyrrolidin-2-one at 64 - 68℃;
potassium phtalimide
1074-82-4

potassium phtalimide

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-benzyl-N,N,N-triethylammonium chloride / N,N-dimethyl-formamide / 6 h / 100 - 120 °C / Industrial scale
2: pyridinium p-toluenesulfonate / toluene / 3 h / Dean-Stark; Reflux; Industrial scale
3: N-Bromosuccinimide / 1,2-dichloro-ethane / 1.33 h / 12 - 22 °C / Industrial scale
4: sodium methylate / toluene; methanol / 5.17 h / 9 - 22 °C / Industrial scale
View Scheme
Multi-step reaction with 4 steps
1: N-benzyl-N,N,N-triethylammonium chloride / N,N-dimethyl-formamide / 6 h / 100 - 120 °C / Industrial scale
2: pyridinium p-toluenesulfonate / toluene / 0.25 h / 30 - 50 °C / Industrial scale
3: chloro-trimethyl-silane / toluene / 2.5 h / 30 °C
4: sodium methylate / methanol / 20 h / 30 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium iodide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C
2.1: hydrogen bromide / 1,2-dichloro-ethane / 4 h / 10 - 15 °C
2.2: 3 h / 0 - 15 °C
View Scheme
(S)-2-(2-methoxy-2-methyl-[1,3]dioxolane-4-ylmethyl)-isoindole-1,3-dione
879507-95-6

(S)-2-(2-methoxy-2-methyl-[1,3]dioxolane-4-ylmethyl)-isoindole-1,3-dione

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chloro-trimethyl-silane / toluene / 2.5 h / 30 °C
2: sodium methylate / methanol / 20 h / 30 °C
View Scheme
(S)-2-phthalimido-1-(chloromethyl)ethyl acetate

(S)-2-phthalimido-1-(chloromethyl)ethyl acetate

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With sodium methylate In methanol at 30℃; for 20h;65.6 kg
1H-isoindole-1,3(2H)-dione, 2-[[(4S)-2-phenyl-1,3-dioxolan-4-yl]methyl]

1H-isoindole-1,3(2H)-dione, 2-[[(4S)-2-phenyl-1,3-dioxolan-4-yl]methyl]

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / 1,2-dichloro-ethane / 1.33 h / 12 - 22 °C / Industrial scale
2: sodium methylate / toluene; methanol / 5.17 h / 9 - 22 °C / Industrial scale
View Scheme
1H-isoindole-1,3(2H)-dione, 2-[(2S)-2,3-dihydroxypropyl]
119835-88-0

1H-isoindole-1,3(2H)-dione, 2-[(2S)-2,3-dihydroxypropyl]

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridinium p-toluenesulfonate / toluene / 3 h / Dean-Stark; Reflux; Industrial scale
2: N-Bromosuccinimide / 1,2-dichloro-ethane / 1.33 h / 12 - 22 °C / Industrial scale
3: sodium methylate / toluene; methanol / 5.17 h / 9 - 22 °C / Industrial scale
View Scheme
Multi-step reaction with 3 steps
1: pyridinium p-toluenesulfonate / toluene / 0.25 h / 30 - 50 °C / Industrial scale
2: chloro-trimethyl-silane / toluene / 2.5 h / 30 °C
3: sodium methylate / methanol / 20 h / 30 °C
View Scheme
2-oxiranylmethylisoindole-1,3-dione
5455-98-1

2-oxiranylmethylisoindole-1,3-dione

A

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
181140-34-1

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione

B

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With Cu metal organic framework based on (R)-3,3′-bis(6-carboxy-2-naphthyl)-2,2′-dihydroxy-1,1′-binaphthyl*silica packed stainless steel column (10 cm long × 4.0 mm i.d.) In ethanol; hexane at 25℃; Resolution of racemate;
2-((S)-3-bromo-2-hydroxypropyl)isoindoline-1,3-dione

2-((S)-3-bromo-2-hydroxypropyl)isoindoline-1,3-dione

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With sodium methylate In methanol; toluene at 5℃; for 0.75h;34.1 g
2-((S)-3-p-toluenesulfonyloxy-2-hydroxypropyl)isoindoline-1,3-dione

2-((S)-3-p-toluenesulfonyloxy-2-hydroxypropyl)isoindoline-1,3-dione

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With sodium methylate In methanol; toluene at -5 - 20℃; for 1.25h;35.8 g
N-(tert-butoxycarbonyl)-1,4-phenylenediamine
71026-66-9

N-(tert-butoxycarbonyl)-1,4-phenylenediamine

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

C22H25N3O5
1082937-55-0

C22H25N3O5

Conditions
ConditionsYield
In isopropyl alcohol for 16h; Reflux;100%
In isopropyl alcohol for 16h; Reflux;100%
In isopropyl alcohol for 16h; Heating / reflux;100%
N-benzyl-2,2-dimethoxyethylamine
54879-88-8

N-benzyl-2,2-dimethoxyethylamine

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

(R)-2-{3-[benzyl-(2,2-dimethoxyethyl)amino]-2-hydroxypropyl}-1H-isoindole-1,3(2H)-dione
1374982-07-6

(R)-2-{3-[benzyl-(2,2-dimethoxyethyl)amino]-2-hydroxypropyl}-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
In ethanol for 20h; Inert atmosphere; Reflux;100%
(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

2-((R)-3-Azido-2-hydroxy-propyl)-isoindole-1,3-dione

2-((R)-3-Azido-2-hydroxy-propyl)-isoindole-1,3-dione

Conditions
ConditionsYield
With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 80℃; for 1h;100%
With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 80℃;100%
3-fluoro-4-(morpholin-4-yl)-phenyl isocyanate
224323-51-7

3-fluoro-4-(morpholin-4-yl)-phenyl isocyanate

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione
168828-89-5

2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions
ConditionsYield
With lithium bromide at 120℃; for 4h; Temperature; Solvent;96.51%
With lithium bromide In N,N-dimethyl-formamide at 60℃; for 4h; Reagent/catalyst; Solvent;90.11%
4-(4-isocyanatophenyl)morpholin-3-one
1325210-64-7

4-(4-isocyanatophenyl)morpholin-3-one

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione
446292-08-6

2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With 3-methyl-1-butyl acetate; magnesium chloride at 120℃; for 4h; Solvent; Reagent/catalyst; Temperature;95.5%
With lithium iodide In chlorobenzene at 115℃; for 4h; Reagent/catalyst; Solvent; Temperature;94.09%
(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

4-(4-aminophenyl)morpholin-3-one
438056-69-0

4-(4-aminophenyl)morpholin-3-one

2-((2R)-2-hydroxy-3-{[4-(3-oxo-4-morpholinyl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione
446292-07-5

2-((2R)-2-hydroxy-3-{[4-(3-oxo-4-morpholinyl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
In ethanol; water at 20℃; for 15h; Solvent; Temperature;95%
In ethanol; water for 27h; Heating;92%
In methanol; water at 65 - 70℃; for 32h;92%
(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

4-(4-aminophenyl)morpholin-3-one
438056-69-0

4-(4-aminophenyl)morpholin-3-one

2-((2R)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione

2-((2R)-2-hydroxy-3-{[4-(3-oxomorpholin-4-yl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
In water; toluene at 30 - 85℃; Solvent; Temperature;94.6%
3-fluoro-4-(morpholinyl)aniline
93246-53-8

3-fluoro-4-(morpholinyl)aniline

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

N-[3-phthalimido-2-(R)-hydroxypropyl]-3-fluoro-4-(4-morpholinyl)aniline
874340-08-6

N-[3-phthalimido-2-(R)-hydroxypropyl]-3-fluoro-4-(4-morpholinyl)aniline

Conditions
ConditionsYield
In ethanol; water at 80℃; for 14h;94.4%
In N,N-dimethyl-formamide for 5h; Product distribution / selectivity; Heating / reflux;
In N,N-dimethyl-formamide
N-acetyl-p-phenylenediamine
122-80-5

N-acetyl-p-phenylenediamine

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

C19H19N3O4

C19H19N3O4

Conditions
ConditionsYield
In isopropyl alcohol for 16h; Reflux;93.8%
(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione
148857-42-5

2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione

Conditions
ConditionsYield
Stage #1: (S)-N-glycidylphthalimide With Chloroiodomethane In 2-methyltetrahydrofuran at -78℃; for 0.0333333h;
Stage #2: With methyllithium In 2-methyltetrahydrofuran; diethyl ether at -78℃; for 1h; Solvent; Reagent/catalyst; Temperature; enantioselective reaction;
93%
With C25H21OP; trichloroacetonitrile In water; N,N-dimethyl-formamide at 25℃; for 6h; Inert atmosphere; Irradiation;78%
4-nitro-aniline
100-01-6

4-nitro-aniline

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

C17H15N3O5

C17H15N3O5

Conditions
ConditionsYield
In ethanol at 50℃; Solvent; Temperature;91%
(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

C11H10INO3

C11H10INO3

Conditions
ConditionsYield
Stage #1: (S)-N-glycidylphthalimide With diiodomethane In 2-methyltetrahydrofuran at -78℃; for 0.0333333h;
Stage #2: With methyllithium In 2-methyltetrahydrofuran; diethyl ether at -78℃; for 1h; enantioselective reaction;
91%
3-fluoro-4-(morpholinyl)aniline
93246-53-8

3-fluoro-4-(morpholinyl)aniline

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

C21H22FN3O4

C21H22FN3O4

Conditions
ConditionsYield
In ethanol at 60℃; for 16h; Temperature; Inert atmosphere;90.09%
(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

2-((S)-3-bromo-2-hydroxypropyl)isoindoline-1,3-dione

2-((S)-3-bromo-2-hydroxypropyl)isoindoline-1,3-dione

Conditions
ConditionsYield
Stage #1: (S)-N-glycidylphthalimide With iodobromomethane In 2-methyltetrahydrofuran at -78℃; for 0.0333333h;
Stage #2: With methyllithium In 2-methyltetrahydrofuran; diethyl ether at -78℃; for 1h; enantioselective reaction;
89%
C10H8(2)H4N2O2

C10H8(2)H4N2O2

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

C21H17(2)H4N3O5

C21H17(2)H4N3O5

Conditions
ConditionsYield
In ethanol; water at 0℃; for 32h; Reflux;88%
2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

(S)-4-(1,3-dioxoisoindol-2-yl)-3-hydroxybutyronitrile
929281-94-7

(S)-4-(1,3-dioxoisoindol-2-yl)-3-hydroxybutyronitrile

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 75℃;87%
phenyl isocyanate
103-71-9

phenyl isocyanate

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

(S)-2-((2-oxo-3-phenyloxazolidin-5-yl)methyl)isoindoline-1,3-dione

(S)-2-((2-oxo-3-phenyloxazolidin-5-yl)methyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With (2-hydroxy-5-methylphenyl)triphenylphosphonium iodide In chlorobenzene at 100℃; for 6h; Inert atmosphere;87%
methyl (3-fluoro-4-morpholinophenyl)carbamate
212325-40-1

methyl (3-fluoro-4-morpholinophenyl)carbamate

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione
168828-89-5

2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions
ConditionsYield
With lithium tert-butoxide In N,N-dimethyl-formamide at 25 - 85℃; Temperature; Solvent; Reagent/catalyst;85%
With lithium tert-butoxide In ethyl acetate at 25 - 75℃; Solvent; Temperature; Reagent/catalyst;70%
(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

(R)-2-(2-hydroxy-3-((4-iodophenyl)amino)propyl)isoindolin-1,3-one

(R)-2-(2-hydroxy-3-((4-iodophenyl)amino)propyl)isoindolin-1,3-one

Conditions
ConditionsYield
In ethanol; water at 100℃; for 12h;84.9%
C24H26N2O3

C24H26N2O3

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

C35H35N3O6

C35H35N3O6

Conditions
ConditionsYield
In methanol; ethanol at 75℃; for 48h; Temperature; Solvent;84.7%
(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-(3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropylamino)benzonitrile
1261131-68-3

4-(3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropylamino)benzonitrile

Conditions
ConditionsYield
at 105℃; for 13h;84%
With magnesium(II) perchlorate In 1,4-dioxane for 10h; Reflux;78%
(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

dibenzylamine
103-49-1

dibenzylamine

2-[(2R)-3-(dibenzylamino)-2-hydroxy-propyl]isoindoline-1,3-dione
1357474-57-7

2-[(2R)-3-(dibenzylamino)-2-hydroxy-propyl]isoindoline-1,3-dione

Conditions
ConditionsYield
In isopropyl alcohol at 0℃; for 9h; Reflux; Inert atmosphere; regioselective reaction;84%
benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate
168828-81-7, 1027135-00-7

benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione
168828-89-5

2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions
ConditionsYield
Stage #1: benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate With lithium tert-butoxide In tetrahydrofuran; N,N-dimethyl-formamide at 5℃; for 0.5h; Inert atmosphere;
Stage #2: (S)-N-glycidylphthalimide In tetrahydrofuran; N,N-dimethyl-formamide at 5 - 20℃; for 24h; Reagent/catalyst; Temperature; Inert atmosphere;
84%
7-fluoro-1-(piperazin-1-yl)isoquinoline

7-fluoro-1-(piperazin-1-yl)isoquinoline

(S)-N-glycidylphthalimide
161596-47-0

(S)-N-glycidylphthalimide

2-[(2R)-3-[4-(7-fluoroisoquinolin-1-yl)piperazin-1-yl]-2-hydroxypropyl]-2,3-dihydro-1H-isoindole-1,3-dione

2-[(2R)-3-[4-(7-fluoroisoquinolin-1-yl)piperazin-1-yl]-2-hydroxypropyl]-2,3-dihydro-1H-isoindole-1,3-dione

Conditions
ConditionsYield
In acetonitrile at 70℃; for 6h;84%

161596-47-0Relevant articles and documents

Novel series of highly potent non-peptide growth hormone secretagogues with improved bioavailability

Ishige, Hirohide,Ishiyama, Nobuo,Mimura, Mitsuo,Hayashida, Mitsuo,Okuno, Tadashi,Ukai, Kiyoharu,Kiyofuji, Takeshi,Yoneda, Yasuo,Tauchi, Shinji,Aoyama, Akinori,Inoguchi, Kiyoshi

, p. 561 - 566 (2006)

The discovery and the SAR of acylproline derivatives as highly potent growth hormone secretagogues (GHSs) with good oral bioavailability are described. One representative compound, N-[3-(2,2-dimethylpropylamino)-2-hydroxypropyl]-2(R)-[1-(2,2-dimethylpropionyl)pyrrolidine-2(S)- carbonylamino]-3-naphthalen-2-ylpropionamide (4e), showed potent GHS activity (ED50=1 nM) and good oral bioavailability (BA=33.2%). Moreover, the optically pure N-[3-(2,2-dimethylpropylamino)-2(S)-hydroypropyl]-2(R)-[1-(2,2-dimethylpropionyl)pyrrolidine-2(S)-carbonylamino]-3-naphthalen-2- ylpropionamide ((2S)-4e) showed a good metabolic stability against in vitro clearance (human liver microsome) with potent GHS activity.

Preparation method of rivaroxaban intermediate

-

Paragraph 0057-0065, (2020/05/02)

The invention provides a preparation method of a rivaroxaban intermediate. The preparation method comprises: (1) carrying out a reaction on a compound A and a compound B in an alcohol or an alcohol aqueous solution to obtain a compound C; and (2) reacting the compound C with N,N'-carbonyldiimidazole in a reaction solvent selected from acetonitrile or butyronitrile to obtain a reaction solution containing a compound D, and performing cooling crystallization to obtain a compound D.

A novel homochiral metal-organic framework with an expanded open cage based on (: R)-3,3′-bis(6-carboxy-2-naphthyl)-2,2′-dihydroxy-1,1′-binaphthyl: synthesis, X-ray structure and efficient HPLC enantiomer separation

Tanaka, Koichi,Kawakita, Tomohiro,Morawiak, Maja,Urbanczyk-Lipkowska, Zofia

, p. 487 - 493 (2019/01/21)

A new homochiral metal-organic framework (MOF) with an expanded open cage based on the (R)-3,3′-bis(6-carboxy-2-naphthyl)-2,2′-dihydroxy-1,1′-binaphthyl ligand was synthesized and utilized as a novel chiral stationary phase for high-performance liquid chromatography. Twelve racemates including sec-alcohols, sulfoxides, epoxides, lactone, 1,3-dioxolan-2-one, and oxazolidinone were used as analytes for evaluating the separation properties of the chiral-MOF-packed column. Experimentally, the homochiral MOF offered good molecular recognition ability, which suggests good prospects for the application of chiral MOFs as stationary phases for enantioseparation.

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