Chloroacetyl chloride → 1-Methoxycarbonyl-3-(2-chloroacetamidophenyl)thiourea

HRID 1415637Notes

Reaction equation

HRID 1415637 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15])=[S:7])=[O:4].[Cl:16][CH2:17][C:18](Cl)=[O:19]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:18](=[O:19])[CH2:17][Cl:16])=[S:7])=[O:4]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 3032830Thiophamine

Product 1

HCID 214518911-Methoxycarbonyl-3-(2-chloroacetamidophenyl)thioureaYield 66.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 1-methoxycarbonyl-3-(2-aminophenyl)thiourea (9.00 g) in toluene (80 ml) was treated with chloroacetyl chloride (4.52 g) at room temperature and the mixture was heated to reflux for 1 hour with stirring. The mixture was then cooled to room temperature and the resultant white solid was filtered off and recrystallised from ethanol to give 1-methoxycarbonyl-3-(2-chloroacetamidophenyl)thiourea (7.98 g ), m.p. 156°-158° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. filtrationthe resultant white solid was filtered off
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-030fd346e1674918adc5150c7679e8fb
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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