2-Mercaptoacetamide → 5-Chloro-5-cyano-3-thiapentanamide

HRID 465680Notes

Reaction equation

HRID 465680 reaction equation
[SH:1][CH2:2][C:3]([NH2:5])=[O:4].[Cl:6][C:7](=[CH2:10])[C:8]#[N:9]>N1C=CC=CC=1>[Cl:6][CH:7]([C:8]#[N:9])[CH2:10][S:1][CH2:2][C:3]([NH2:5])=[O:4]

Participants

4

Reactant 2

HCID 129612-MercaptoacetamideHCID 701982-Chloroacrylonitrile

Product 1

HCID 109541055-Chloro-5-cyano-3-thiapentanamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-mercaptoacetamide (20 g) in dry pyridine (80 ml) was stirred whilst 2-chloroacrylonitrile (18 ml) was added slowly with ice-bath cooling. After the addition was complete, the ice-bath was removed, and the mixture was stirred for 45 minutes. The resultant mixture contained the title compound. A portion of the mixture was shaken repeatedly with petroleum ether (b.p. 60° to 80° C.) to leave the title compound as a syrup. 'H nmr δ (CD3COCD3) 5.50 (1H,t,J=7HZ, CH2CH), 3.40 (2H, d,J=7HZ, CH2CH), 3.50(2H, s, CH2CN).

Workup

  1. additionwas added slowly with ice-bath
  2. temperaturecooling
  3. additionAfter the addition
  4. customthe ice-bath was removed
  5. stirringA portion of the mixture was shaken repeatedly with petroleum ether (b.p. 60° to 80° C.)

Sources & evidence

ORD record
ord-947f5c2c5f8d422fa3cd0b9230cc645f
Source dataset
uspto-grants-1992_10
Patent number
US05153330

Reaction notes

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