2-Aminothiophenol → N-acetyl-S-(2-aminophenyl)cysteine

HRID 1719100Notes

Reaction equation

HRID 1719100 reaction equation
[C:1]([NH:4][C:5](=[CH2:9])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[SH:17]>C(O)C>[C:1]([NH:4][C@H:5]([C:6]([OH:8])=[O:7])[CH2:9][S:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH2:10])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 794822-Acetamidoacrylic acid

Product 1

HCID 57145208N-acetyl-S-(2-aminophenyl)cysteineYield 52.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture consisting of 8.6 g of α-acetylaminoacrylic acid, 20 g of 2-aminobenzenethiol and 50 ml of ethanol was heated for an hour. After the ethanol was distilled off, ether was added to the residue so as to cause crystallization. Upon recrystallization from ethanol, there was obtained 8.9 g of the desired product. Its melting point (m.p.) was 143°-144° C.

Workup

  1. temperaturewas heated for an hour
  2. distillationAfter the ethanol was distilled off
  3. additionether was added to the residue so as
  4. customcrystallization
  5. customUpon recrystallization from ethanol

Sources & evidence

ORD record
ord-2177be98f64e40c1ba4d7bf05c903e50
Source dataset
uspto-grants-1985_09
Patent number
US04539151

Reaction notes

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