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89-33-8

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89-33-8 Usage

Chemical Properties

light yellow crystalline powder

Check Digit Verification of cas no

The CAS Registry Mumber 89-33-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 9 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 89-33:
(4*8)+(3*9)+(2*3)+(1*3)=68
68 % 10 = 8
So 89-33-8 is a valid CAS Registry Number.
InChI:InChI=1/C12H12N2O3/c1-2-17-12(16)10-8-11(15)14(13-10)9-6-4-3-5-7-9/h3-7H,2,8H2,1H3

89-33-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl 5-oxo-1-phenyl-2-pyrazoline-3-carboxylate

1.2 Other means of identification

Product number -
Other names CARBETHOXYPYRAZOLONE

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:89-33-8 SDS

89-33-8Synthetic route

C6H6N2*(x)ClH

C6H6N2*(x)ClH

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

Conditions
ConditionsYield
Stage #1: C6H6N2*(x)ClH With sodium acetate In ethanol; water at 20℃; for 0.0833333h;
Stage #2: acetylenedicarboxylic acid diethyl ester In ethanol; water for 3h; Reflux;
C16H9BrFNOS

C16H9BrFNOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(2-bromo-6-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(2-bromo-6-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H9BrFNOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With quinine In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Michael Addition; enantioselective reaction;
96%
C16H10N2O3S

C16H10N2O3S

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(4-nitrophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(4-nitrophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H10N2O3S; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
96%
C16H10ClNOS

C16H10ClNOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(3-chlorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(3-chlorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H10ClNOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With quinine In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Michael Addition; enantioselective reaction;
95%
C16H10FNOS

C16H10FNOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(2-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(2-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H10FNOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With quinine In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Michael Addition; enantioselective reaction;
94%
C16H10FNOS

C16H10FNOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(2-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(2-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H10FNOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
94%
C16H10FNOS

C16H10FNOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(3-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(3-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H10FNOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With quinine In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Michael Addition; enantioselective reaction;
94%
C16H10N2O3S

C16H10N2O3S

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(4-nitrophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(4-nitrophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H10N2O3S; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With quinine In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Michael Addition; enantioselective reaction;
93%
C17H13NOS

C17H13NOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(m-tolyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(m-tolyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C17H13NOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With quinine In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Michael Addition; enantioselective reaction;
92%
C16H10FNOS

C16H10FNOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(3-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(3-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H10FNOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
91%
C16H10BrNOS

C16H10BrNOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(4-bromophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(4-bromophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H10BrNOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With quinine In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Michael Addition; enantioselective reaction;
91%
5-benzylidene thiazolone
92795-17-0

5-benzylidene thiazolone

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(phenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(phenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: 5-benzylidene thiazolone; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With quinine In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Reagent/catalyst; Solvent; Michael Addition; enantioselective reaction;
91%
C16H10ClNOS

C16H10ClNOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(3-chlorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(3-chlorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H10ClNOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
90%
C16H9BrFNOS

C16H9BrFNOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(2-bromo-6-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(2-bromo-6-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H9BrFNOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
90%
5-benzylidene thiazolone
92795-17-0

5-benzylidene thiazolone

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(phenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(phenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: 5-benzylidene thiazolone; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
89%
C16H10FNOS

C16H10FNOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(4-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(4-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H10FNOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
88%
C17H13NOS

C17H13NOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(p-tolyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(p-tolyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C17H13NOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
87%
C16H10BrNOS

C16H10BrNOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(4-bromophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(4-bromophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H10BrNOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
86%
C18H15NOS

C18H15NOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(2,4-dimethylphenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(2,4-dimethylphenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C18H15NOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
85%
5-benzylidene thiazolone
92795-17-0

5-benzylidene thiazolone

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(phenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(phenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: 5-benzylidene thiazolone; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With 3-(3,5-bis(trifluoromethyl)anilino)-4-([(1R,2R)-2-(piperidin-1-yl)cyclohexyl]amino)cyclobut-3-ene-1,2-dione In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Michael Addition; enantioselective reaction;
85%
C16H10FNOS

C16H10FNOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(4-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(4-fluorophenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C16H10FNOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With quinine In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Michael Addition; enantioselective reaction;
83%
C17H13NOS

C17H13NOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(m-tolyl)methyl)-1-phenyl-1H- pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(m-tolyl)methyl)-1-phenyl-1H- pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C17H13NOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
83%
C22H15NOS

C22H15NOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 4-([1,1'-biphenyl]-4-yl(4-acetoxy-2-phenylthiazol-5-yl)methyl)-5-acetoxy-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 4-([1,1'-biphenyl]-4-yl(4-acetoxy-2-phenylthiazol-5-yl)methyl)-5-acetoxy-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C22H15NOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With quinine In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Michael Addition; enantioselective reaction;
81%
C17H13NOS

C17H13NOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(o-tolyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(o-tolyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C17H13NOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With quinine In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Michael Addition; enantioselective reaction;
80%
C22H15NOS

C22H15NOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 4-([1,1'-biphenyl]-4-yl(4-acetoxy-2-phenylthiazol-5-yl)methyl)-5-acetoxy-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 4-([1,1'-biphenyl]-4-yl(4-acetoxy-2-phenylthiazol-5-yl)methyl)-5-acetoxy-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C22H15NOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
79%
C17H13NOS

C17H13NOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(o-tolyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(o-tolyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C17H13NOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
79%
N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-chloro-4-formyl-1-phenyl-1H-pyrazole-3-carboxylate
38405-71-9

ethyl 5-chloro-4-formyl-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
With trichlorophosphate at 10 - 70℃; Vilsmeier-Haack reaction;78%
C18H15NOS

C18H15NOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(2,4-dimethylphenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(2,4-dimethylphenyl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C18H15NOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With quinine In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Michael Addition; enantioselective reaction;
78%
C20H13NOS

C20H13NOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(naphthalen-2-yl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(naphthalen-2-yl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C20H13NOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With quinine In dichloromethane at 30℃; for 24h; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; for 0.5h; Michael Addition; enantioselective reaction;
75%
C20H13NOS

C20H13NOS

acetyl chloride
75-36-5

acetyl chloride

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(naphthalen-2-yl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

ethyl 5-acetoxy-4-((4-acetoxy-2-phenylthiazol-5-yl)(naphthalen-2-yl)methyl)-1-phenyl-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
Stage #1: C20H13NOS; 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one With potassium carbonate In dichloromethane at 20℃; Michael Addition;
Stage #2: acetyl chloride In dichloromethane at 0℃; Michael Addition;
71%
2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one
89-33-8

2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one

[1-chloro-2,2,2-trifluoro-1-(4-methoxy-phenyl)-ethyl]-p-tolyl-carbodiimide

[1-chloro-2,2,2-trifluoro-1-(4-methoxy-phenyl)-ethyl]-p-tolyl-carbodiimide

4-(4-methoxy-phenyl)-1-phenyl-6-p-tolylimino-4-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[4,3-e][1,3]oxazine-3-carboxylic acid ethyl ester

4-(4-methoxy-phenyl)-1-phenyl-6-p-tolylimino-4-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[4,3-e][1,3]oxazine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 2,4-dihydro-2-phenyl-5-ethoxycarbonyl-3H-pyrazol-3-one; [1-chloro-2,2,2-trifluoro-1-(4-methoxy-phenyl)-ethyl]-p-tolyl-carbodiimide With triethylamine In benzene at 20℃; for 2h;
Stage #2: In benzene for 2h; Heating;
53%

89-33-8Downstream Products

89-33-8Relevant articles and documents

Catalytic System-Controlled Divergent Reaction Strategies for the Construction of Diversified Spiropyrazolone Skeletons from Pyrazolidinones and Diazopyrazolones

Fang, Feifei,Han, Xu,Hu, Shulei,Li, Chunpu,Liu, Hong,Wang, Qian,Wang, Run,Zhou, Yu

supporting information, p. 21327 - 21333 (2021/08/20)

A catalytic system-controlled divergent reaction strategy was here reported to construct four types of intriguing spiroheterocyclic skeletons from simple and readily available starting materials via a precise chemical bond activation/[n+1] annulation cascade. The tetraazaspiroheterocyclic and trizazspiroheterocyclic scaffolds could be independently constructed by a selective N?N bond activation/[n+1] annulation cascade, a C(sp2)-H activation/[4+1] annulation and a novel tandem C(sp2)-H/C(sp3)?H bond activation/[4+1] annulation strategy, along with a broad scope of substrates, moderate to excellent yields and valuable transformations. More importantly, in these transformations, we are the first time to capture a N?N bond activation and a C(sp3)?H bond activation of pyrazolidinones under different catalytic system.

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