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637-53-6 Usage

Chemical Description

Thioacetanilide is a thioamide compound used in organic synthesis.

Chemical Properties

yellow crystalline powder

General Description

Metabolism and acute toxicity of thioacetanilide has been studied in rat. Thioacetanilide undergoes nucleophilic addition reaction with superoxide ion in dimethyl sulfoxide.

Check Digit Verification of cas no

The CAS Registry Mumber 637-53-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 7 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 637-53:
(5*6)+(4*3)+(3*7)+(2*5)+(1*3)=76
76 % 10 = 6
So 637-53-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NS/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)

637-53-6 Well-known Company Product Price

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  • Aldrich

  • (163651)  Thioacetanilide  98%

  • 637-53-6

  • 163651-10G

  • 1,574.82CNY

  • Detail

637-53-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Thioacetanilide

1.2 Other means of identification

Product number -
Other names Ethanethioamide, N-phenyl-

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:637-53-6 SDS

637-53-6Synthetic route

mercury(II) diacetate
1600-27-7

mercury(II) diacetate

bis(thioacetanilide)mercury(II)

bis(thioacetanilide)mercury(II)

A

thioacetanilide
637-53-6

thioacetanilide

B

N-acetyl-N-phenylacetamide
1563-87-7

N-acetyl-N-phenylacetamide

Conditions
ConditionsYield
In dichloromethane for 3h; Ambient temperature;A n/a
B 100%
Acetanilid
103-84-4

Acetanilid

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With 2,4-bis(4-(5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluorodecyloxy)phenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide In tetrahydrofuran at 55℃; for 6h;97%
With 2,4-{[3-[(CH2)5C8F17]-4-MeO-phenyl]}2-P2S2 2,4-disulfide for 0.05h; microwave irradiation;96%
With Lawessons reagent for 0.0333333h; microwave irradiation;96%
acetophenone oxime
613-91-2

acetophenone oxime

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
Stage #1: acetophenone oxime With triethylamine; p-toluenesulfonyl chloride In acetonitrile at 0 - 20℃; Inert atmosphere;
Stage #2: With thiourea In acetonitrile for 2h; Reflux; Inert atmosphere;
90%
With tetraphosphorus decasulfide In benzene at 80℃; for 0.5h; Beckmann Rearrangement;90%
With trichlorothiophosphine; water; triethylamine at 0 - 75℃; Beckmann rearrangement; chemoselective reaction;78%
acetophenone
98-86-2

acetophenone

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate; O,O-Diethyl hydrogen phosphorodithioate In 1,4-dioxane at 80 - 90℃; for 2h; Inert atmosphere;89%
aniline
62-53-3

aniline

Thioacetic acid S-(5,5-dimethyl-2-thioxo-2λ5-[1,3,2]dioxaphosphinan-2-yl) ester
157841-92-4

Thioacetic acid S-(5,5-dimethyl-2-thioxo-2λ5-[1,3,2]dioxaphosphinan-2-yl) ester

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
Stage #1: Thioacetic acid S-(5,5-dimethyl-2-thioxo-2λ5-[1,3,2]dioxaphosphinan-2-yl) ester With 5,5-dimethyl-2-thiolo-2-thiono-1,3,2-dioxaphosphorinane In benzene for 3h; Heating;
Stage #2: aniline With triethylamine In benzene cooling; Further stages.;
87.8%
aniline
62-53-3

aniline

thioacetic acid
507-09-5

thioacetic acid

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With 1H-imidazole; iodine; chloro-diphenylphosphine In dichloromethane for 0.75h; Reflux;85%
With 1,2-bis(5-methylisoxazol-3-yl)hydrazine; triphenylphosphine In acetonitrile for 4.5h; Mitsunobu reaction; Reflux;83%
morpholine
110-91-8

morpholine

2-thioxo-4-thiazolidinone
141-84-4

2-thioxo-4-thiazolidinone

Acetanilid
103-84-4

Acetanilid

A

2-morpholin-4-yl-2-thiazole-4(5H)-one
16781-67-2

2-morpholin-4-yl-2-thiazole-4(5H)-one

B

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With MCM-41 mesoporous silica In ethanol; water at 80 - 90℃; for 8h; Green chemistry;A n/a
B 70%
methyllithium
917-54-4

methyllithium

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at -78℃; for 0.5h;70%
copper diacetate
142-71-2

copper diacetate

bis(thioacetanilide)mercury(II)

bis(thioacetanilide)mercury(II)

A

thioacetanilide
637-53-6

thioacetanilide

B

N-acetyl-N-phenylacetamide
1563-87-7

N-acetyl-N-phenylacetamide

Conditions
ConditionsYield
In dichloromethane for 120h; Ambient temperature;A n/a
B 59%
acetic acid
64-19-7

acetic acid

aniline
62-53-3

aniline

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With O,O-Diethyl hydrogen phosphorodithioate In toluene for 8h; Heating;51%
C16H16N2S2
10319-73-0

C16H16N2S2

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform at 5℃; for 15h;33%
Lawessons reagent
19172-47-5

Lawessons reagent

N-Phenylacetohydroxamic acid
1795-83-1

N-Phenylacetohydroxamic acid

A

N-hydroxy-N-phenyl-thioacetamide

N-hydroxy-N-phenyl-thioacetamide

B

C15H16NO4PS

C15H16NO4PS

C

thioacetanilide
637-53-6

thioacetanilide

D

Acetanilid
103-84-4

Acetanilid

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 2h; Further byproducts given. Title compound not separated from byproducts;A 5%
B n/a
C 28%
D 50 % Spectr.
(4-acetamidophenyl)disulfide
16766-09-9

(4-acetamidophenyl)disulfide

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
at 240 - 260℃;
N-phenyl-3-thio-malonamic acid
10394-24-8

N-phenyl-3-thio-malonamic acid

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With water Heating;
beim Erhitzen;
dithioacetic acid
594-03-6

dithioacetic acid

phenyl isocyanate
103-71-9

phenyl isocyanate

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With toluene
dithioacetic acid
594-03-6

dithioacetic acid

phenyl isocyanate
103-71-9

phenyl isocyanate

toluene
108-88-3

toluene

A

carbon oxide sulfide
463-58-1

carbon oxide sulfide

B

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
methyl magnesium iodide
917-64-6

methyl magnesium iodide

diethyl ether
60-29-7

diethyl ether

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
durch nachfolgende Behandlung des Reaktionspr. mit Wasser und verd. Schwefelsaeure;
methyl magnesium iodide
917-64-6

methyl magnesium iodide

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With diethyl ether und Behandeln des Aetherrueckstandes mit Eiswasser und verd.Schwefelsaeure;
dithioacetic acid
594-03-6

dithioacetic acid

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With toluene
dithioacetic acid
594-03-6

dithioacetic acid

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

toluene
108-88-3

toluene

A

carbon disulfide
75-15-0

carbon disulfide

B

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
diethyl ether
60-29-7

diethyl ether

N-phenylacetimidoyl chloride
874-69-1

N-phenylacetimidoyl chloride

thioacetamide
62-55-5

thioacetamide

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
reagiert analog mit N-Phenyl-benzimidchlorid;
N-phenylacetimidoyl chloride
874-69-1

N-phenylacetimidoyl chloride

thioacetamide
62-55-5

thioacetamide

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With diethyl ether
diethyl ether
60-29-7

diethyl ether

N-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

benzenecarbothioamide
2227-79-4

benzenecarbothioamide

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
O-Ethyl thioacetate
926-67-0

O-Ethyl thioacetate

diethyl ether
60-29-7

diethyl ether

aniline
62-53-3

aniline

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
O-Ethyl thioacetate
926-67-0

O-Ethyl thioacetate

aniline
62-53-3

aniline

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With diethyl ether
diethyl ether
60-29-7

diethyl ether

N-phenylacetimidoyl chloride
874-69-1

N-phenylacetimidoyl chloride

benzenecarbothioamide
2227-79-4

benzenecarbothioamide

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
N-phenylacetimidoyl chloride
874-69-1

N-phenylacetimidoyl chloride

benzenecarbothioamide
2227-79-4

benzenecarbothioamide

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With diethyl ether
Acetanilid
103-84-4

Acetanilid

A

thioacetanilide
637-53-6

thioacetanilide

B

N,N'-diphenylacetamidine
621-09-0, 141417-91-6, 1086215-03-3

N,N'-diphenylacetamidine

Conditions
ConditionsYield
With tetraphosphorus decasulfide
(E)-1-phenylethanone oxime
10341-75-0

(E)-1-phenylethanone oxime

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
With pyridine beim Behandeln anschliessend mit H2S;
O-Ethyl thioacetate
926-67-0

O-Ethyl thioacetate

anilinomagnesium bromide

anilinomagnesium bromide

thioacetanilide
637-53-6

thioacetanilide

Conditions
ConditionsYield
thioacetanilide
637-53-6

thioacetanilide

Acetanilid
103-84-4

Acetanilid

Conditions
ConditionsYield
With 6H(1+)*Mo9O40PV3(6-); oxygen In acetonitrile at 60℃; under 760.051 Torr; for 0.5h; Inert atmosphere; Glovebox;99%
With eosin; oxygen In N,N-dimethyl-formamide at 20℃; for 6h; Reagent/catalyst; Solvent; Irradiation; Green chemistry;93%
With P,P-dichlorophenylphosphine oxide In acetonitrile at -4℃; for 3h;90%
phenylsulfonyl azide
938-10-3

phenylsulfonyl azide

thioacetanilide
637-53-6

thioacetanilide

N-phenyl-N'-benzenesulfonylacetamidine

N-phenyl-N'-benzenesulfonylacetamidine

Conditions
ConditionsYield
In ethanol for 1h; Temperature; Solvent; Reflux; chemoselective reaction;99%
In ethanol at 20℃; for 20h;63%
thioacetanilide
637-53-6

thioacetanilide

phenylacetylene
536-74-3

phenylacetylene

N-phenyl-N-[(E)-2-phenylvinyl]thioacetamide
1068465-05-3

N-phenyl-N-[(E)-2-phenylvinyl]thioacetamide

Conditions
ConditionsYield
With TOP; bis(2-methallyl)(cycloocta-1,5-diene)ruthenium(II) In toluene at 100℃; for 15h; Molecular sieve; Inert atmosphere;98%
thioacetanilide
637-53-6

thioacetanilide

Methanesulfonyl azide
624-90-8, 1516-70-7

Methanesulfonyl azide

N-phenyl-N'-methanesulfonylacetamidine

N-phenyl-N'-methanesulfonylacetamidine

Conditions
ConditionsYield
In ethanol for 1h; Temperature; Solvent; Reflux; chemoselective reaction;97%
pentacarbonyl[3-(cyclohex-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

pentacarbonyl[3-(cyclohex-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

thioacetanilide
637-53-6

thioacetanilide

syn-pentacarbonyl[N-phenylthioacetimidic acid (3-ethoxy-4,5,6,7-tetrahydro-3aH-inden-1-yl) ester-N]tungsten

syn-pentacarbonyl[N-phenylthioacetimidic acid (3-ethoxy-4,5,6,7-tetrahydro-3aH-inden-1-yl) ester-N]tungsten

Conditions
ConditionsYield
In diethyl ether under Ar atm. pentacarbonyl(3-(cyclohex-1-yl)-1-ethoxy-2-propyn-1-ylidene)tungsten was reacted with (N-phenyl)thioacetamide in diethyl ether at20°C for 25 min; ppt. was collected, washed with n-pentane and dried in vacuo; elem. anal.;96%
thioacetanilide
637-53-6

thioacetanilide

3-(trifluoromethyl)benzenesulfonyl azide

3-(trifluoromethyl)benzenesulfonyl azide

N'-((3-trifluoromethylphenyl)sulfonyl)-N-phenylacetimidamide

N'-((3-trifluoromethylphenyl)sulfonyl)-N-phenylacetimidamide

Conditions
ConditionsYield
In ethanol at 20℃; for 17h;95%
pentacarbonyl[3-(cyclohept-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

pentacarbonyl[3-(cyclohept-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

thioacetanilide
637-53-6

thioacetanilide

syn-pentacarbonyl[N-phenylthioacetimidic acid (3-ethoxy-4,5,6,7,8-pentahydro-3aH-azulen-1-yl) ester-N]tungsten

syn-pentacarbonyl[N-phenylthioacetimidic acid (3-ethoxy-4,5,6,7,8-pentahydro-3aH-azulen-1-yl) ester-N]tungsten

Conditions
ConditionsYield
In diethyl ether under Ar atm. pentacarbonyl(3-(cyclohex-1-yl)-1-ethoxy-2-propyn-1-ylidene)tungsten was reacted with (N-phenyl)thioacetamide in diethyl ether at20°C for 25 min; ppt. was collected, washed with n-pentane and dried in vacuo; elem. anal.;94%
thioacetanilide
637-53-6

thioacetanilide

3,5-bis(trifluoromethyl)phenylsulfonyl azide
1431968-93-2

3,5-bis(trifluoromethyl)phenylsulfonyl azide

N'-((3,5-bis(trifluoromethyl)phenyl)sulfonyl)-N-phenylacetimidamide

N'-((3,5-bis(trifluoromethyl)phenyl)sulfonyl)-N-phenylacetimidamide

Conditions
ConditionsYield
In ethanol at 20℃; for 7h;93%
1,3-diethyl 2-diazopropanedioate
5256-74-6

1,3-diethyl 2-diazopropanedioate

thioacetanilide
637-53-6

thioacetanilide

diethyl 2-(1-(phenylamino)ethylidene)malonate
81022-80-2

diethyl 2-(1-(phenylamino)ethylidene)malonate

Conditions
ConditionsYield
With tris(triphenylphosphine)ruthenium(II) chloride In benzene at 90℃; for 4h; Reagent/catalyst; Time; Inert atmosphere; Sealed tube;92%
With copper(I)-complexed magnetic nanoparticle catalyst In 1,2-dichloro-ethane at 70℃; for 5h;90%
With (CuOTf)2*Tol In 1,2-dichloro-ethane at 90℃; for 9h; Inert atmosphere; Sealed tube;74%
ethyl 2-diazo-3-oxobutanoate
2009-97-4

ethyl 2-diazo-3-oxobutanoate

thioacetanilide
637-53-6

thioacetanilide

2-acetyl-3-phenylaminobut-2-enoic acid ethyl ester

2-acetyl-3-phenylaminobut-2-enoic acid ethyl ester

Conditions
ConditionsYield
With copper(I)-complexed magnetic nanoparticle catalyst In 1,2-dichloro-ethane at 70℃; for 3h; diastereoselective reaction;91%
2-bromo-2-propenoic acid
10443-65-9

2-bromo-2-propenoic acid

thioacetanilide
637-53-6

thioacetanilide

4-carboxy-2-methyl-3-phenyl-Δ2-thiazolinium bromide

4-carboxy-2-methyl-3-phenyl-Δ2-thiazolinium bromide

Conditions
ConditionsYield
In toluene at 90℃; for 1h;90%
In toluene at 90℃;
tetra[μ-acetato-bis(methanol)]dirhodium

tetra[μ-acetato-bis(methanol)]dirhodium

thioacetanilide
637-53-6

thioacetanilide

Rh2(OC2Me)4(N-phenylthioacetamide)2

Rh2(OC2Me)4(N-phenylthioacetamide)2

Conditions
ConditionsYield
In ethanol soln. of ligand added to soln. of Rh-complex with stirring (1 h);; filtered, washed with absolute EtOH, dried in vacuo, washed with abundant pentane, elem. anal.;;90%
[(Fe(CO)3)2(μ-S(Me)C(CF3)CFC(NMe2))]

[(Fe(CO)3)2(μ-S(Me)C(CF3)CFC(NMe2))]

thioacetanilide
637-53-6

thioacetanilide

[(Fe(CO)3)2( μ-S(CH3)C(CF3)C β (SC(NPh)Me) C α (N(CH3)2))]
436162-62-8

[(Fe(CO)3)2( μ-S(CH3)C(CF3)C β (SC(NPh)Me) C α (N(CH3)2))]

Conditions
ConditionsYield
In tetrahydrofuran room temp., 3 hs, (Ar); filtration (celite), vac. evapn., washing (-50 °C, pentane), elem. anal.;90%
pentacarbonyl[3-(cyclopent-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

pentacarbonyl[3-(cyclopent-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

thioacetanilide
637-53-6

thioacetanilide

pentacarbonyl[N-phenyl-thioacetimidic acid (3-ethoxy-2,4,5,6-tetrahydropentalen-1-yl) ester-N]tungsten

pentacarbonyl[N-phenyl-thioacetimidic acid (3-ethoxy-2,4,5,6-tetrahydropentalen-1-yl) ester-N]tungsten

Conditions
ConditionsYield
With triethylamine In dichloromethane under Ar atm. pentacarbonyl(3-(cyclopent-1-yl)-1-ethoxy-2-propyn-1-ylidene)tungsten was reacted with (N-phenyl)thioacetamide in dichloromethanein the presence of 1 equiv. triethylamine with stirring for 20 min at 20°C; fast chromy. on silica; elem. anal.;89%
thioacetanilide
637-53-6

thioacetanilide

1-chloro-1-phenyl-2,2,2-trifluoroethyl isocyanate
57959-52-1

1-chloro-1-phenyl-2,2,2-trifluoroethyl isocyanate

6-Methylene-2,5-diphenyl-2-trifluoromethyl-[1,3,5]thiadiazinan-4-one

6-Methylene-2,5-diphenyl-2-trifluoromethyl-[1,3,5]thiadiazinan-4-one

Conditions
ConditionsYield
With triethylamine In benzene for 3h;88%
thioacetanilide
637-53-6

thioacetanilide

5-methyl-1-phenyl-1H-tetrazole
14213-16-2

5-methyl-1-phenyl-1H-tetrazole

Conditions
ConditionsYield
With sodium azide; tetrachlorosilane In acetonitrile at 20 - 82℃; for 6h;87%
N-nitrosoacetanilide
938-81-8

N-nitrosoacetanilide

thioacetanilide
637-53-6

thioacetanilide

A

2,2'-dipyridyldisulphide
2127-03-9

2,2'-dipyridyldisulphide

B

N-Phenyl-thioacetimidic acid phenyl ester
87107-49-1

N-Phenyl-thioacetimidic acid phenyl ester

C

Acetanilid
103-84-4

Acetanilid

Conditions
ConditionsYield
Product distribution;A 86%
B 71%
C 75%
pentacarbonyl[3-(cyclohept-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

pentacarbonyl[3-(cyclohept-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

thioacetanilide
637-53-6

thioacetanilide

pentacarbonyl[N-phenylthioacetimidic acid (3-ethoxy-4,5,6,7,8-pentahydro-3aH-azulen-1-yl) ester-N]tungsten

pentacarbonyl[N-phenylthioacetimidic acid (3-ethoxy-4,5,6,7,8-pentahydro-3aH-azulen-1-yl) ester-N]tungsten

Conditions
ConditionsYield
With triethylamine In dichloromethane under Ar atm. pentacarbonyl(3-(cyclohept-1-yl)-1-ethoxy-2-propyn-1-ylidene)tungsten was reacted with (N-phenyl)thioacetamide in dichloromethanein the presence of 1 equiv. triethylamine with stirring for 20 min at 20°C; elem. anal.;86%
di(rhodium)tetracarbonyl dichloride

di(rhodium)tetracarbonyl dichloride

thioacetanilide
637-53-6

thioacetanilide

{Rh2(CO)4(μ-CH3CSN(C6H5))2}

{Rh2(CO)4(μ-CH3CSN(C6H5))2}

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran byproducts: H2; addn. of N-phenylacetamide to a stirred suspn. of NaH (THF), filtn. of soln. into a stirred soln. of starting Rh-complex (THF, -78°C), all steps under N2; evapg. to dryness, extg. of residue (hexane), concg., cooling to 0°C, elem. anal.;84%
With triethylamine In not given
thioacetanilide
637-53-6

thioacetanilide

3-nitrobenzenesulfonyl azide
6647-85-4

3-nitrobenzenesulfonyl azide

N'-((3-nitrophenyl)sulfonyl)-N-phenylacetimidamide

N'-((3-nitrophenyl)sulfonyl)-N-phenylacetimidamide

Conditions
ConditionsYield
In ethanol at 20℃; for 20h;84%
pentacarbonyl[3-(cyclohex-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

pentacarbonyl[3-(cyclohex-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

thioacetanilide
637-53-6

thioacetanilide

pentacarbonyl[N-phenylthioacetimidic acid (3-ethoxy-4,5,6,7-tetrahydro-3aH-inden-1-yl) ester-N]tungsten

pentacarbonyl[N-phenylthioacetimidic acid (3-ethoxy-4,5,6,7-tetrahydro-3aH-inden-1-yl) ester-N]tungsten

Conditions
ConditionsYield
With triethylamine In dichloromethane under Ar atm. pentacarbonyl(3-(cyclohex-1-yl)-1-ethoxy-2-propyn-1-ylidene)tungsten was reacted with (N-phenyl)thioacetamide in dichloromethane in the presence of 1 equiv. triethylamine with stirring for 20 min at 20°C; elem. anal.;83%
thioacetanilide
637-53-6

thioacetanilide

acetic acid hydrazide
1068-57-1

acetic acid hydrazide

3,5-dimethyl-4-phenyl-4H-[1,2,4]triazole
13576-46-0

3,5-dimethyl-4-phenyl-4H-[1,2,4]triazole

Conditions
ConditionsYield
With mercury(II) diacetate In tetrahydrofuran microwave irradiation;82%
In butan-1-ol for 16h; Heating; Yield given;
(–)-menthone

(–)-menthone

thioacetanilide
637-53-6

thioacetanilide

2-[(1R,2S,5R)-1-hydroxy-5-methyl-2-(propan-2-yl)cyclohexyl]-N-phenylethanethioamide

2-[(1R,2S,5R)-1-hydroxy-5-methyl-2-(propan-2-yl)cyclohexyl]-N-phenylethanethioamide

Conditions
ConditionsYield
Stage #1: thioacetanilide With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran at -5 - 5℃; for 1.5h; Inert atmosphere;
Stage #2: (–)-menthone In tetrahydrofuran at -15 - -5℃; Inert atmosphere; stereoselective reaction;
81%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

thioacetanilide
637-53-6

thioacetanilide

N-phenyl-N'-tosylacetimidamide
27049-62-3

N-phenyl-N'-tosylacetimidamide

Conditions
ConditionsYield
In pyridine at 90 - 100℃; for 5h;79%
In ethanol at 20℃; for 20h;46%

637-53-6Relevant articles and documents

Contribution of Solvents to Geometrical Preference in the Z/ E Equilibrium of N-Phenylthioacetamide

Chan, Erika S.,Hyodo, Tadashi,Ikeda, Hirotaka,Inagaki, Satoshi,Ohwada, Tomohiko,Otani, Yuko,Song, Shuyi,Tang, Yulan,Vu, Kim Anh L.,Yamaguchi, Kentaro

, (2021/06/28)

We studied the Z/E preference of N-phenylthioacetamide (thioacetanilide) derivatives in various solvents by means of 1H NMR spectroscopy, as well as molecular dynamics (MD) and other computational analyses. Our experimental results indicate that the Z/E isomer preference of secondary (NH)thioamides of N-phenylthioacetamides shows substantial solvent dependency, whereas the corresponding amides do not show solvent dependency of the Z/E isomer ratios. Detailed study of the solvent effects based on molecular dynamics simulations revealed that there are two main modes of hydrogen (H)-bond formation between solvent and (NH)thioacetamide, which influence the Z/E isomer preference of (NH)thioamides. DFT calculations of NH-thioamide in the presence of one or two explicit solvent molecules in the continuum solvent model can effectively mimic the solvation by multiple solvent molecules surrounding the thioamide in MD simulations and shed light on the precise nature of the interactions between thioamide and solvent. Orbital interaction analysis showed that, counterintuitively, the Z/E preference of NH-thioacetamides is mainly determined by steric repulsion, while that of sterically congested N-methylthioacetamides is mainly determined by thioamide conjugation.

Iodoalkyne-Based Catalyst-Mediated Activation of Thioamides through Halogen Bonding

Matsuzawa, Akinobu,Takeuchi, Shiho,Sugita, Kazuyuki

supporting information, p. 2863 - 2866 (2016/10/25)

Halogen bonding catalysis has recently gained increasing attention as a powerful tool to activate organic molecules. However, the variety of the catalyst structure has been quite limited so far. Herein, we report the first example of the use of an iodoalkyne as a halogen bond donor catalyst. By using an iodoalkyne bearing a pentafluorophenyl group as a catalyst, thioamides were efficiently activated and reacted with 2-aminophenol to generate benzoxazoles in good yield. Mechanistic studies, including 13C NMR spectroscopic analysis and several control experiments, provided concrete evidence that this catalytic activation is based on halogen bonding. Thus, the results obtained in this study demonstrate that iodoalkynes can serve as a new scaffold for future development of halogen bonding catalysis.

Transamidation of thioacetamide catalyzed by SbCl3

Ojeda-Porras, Andrea,Gamba-Sánchez, Diego

supporting information, p. 4308 - 4311 (2015/06/22)

A transamidation reaction of thioacetamide with primary and secondary amines is described. The use of catalytic amounts of SbCl3 notably increases the yields and diminishes the reaction times. Typically, the amines should be aliphatic, but aromatic amines can be used as well, though with lower yields. This is one of the few examples where antimony has been used as a catalyst in organic reactions.

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