2-Thiopheneacetyl chloride → Methyl 4-chloro-5-nitro-2-(2-(thiophen-2-yl)acetamido)benzoate

HRID 1858165Notes

Reaction equation

HRID 1858165 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Cl:13])=[CH:6][C:5]=1[NH2:14].[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH2:21][C:22](Cl)=[O:23]>>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Cl:13])=[CH:6][C:5]=1[NH:14][C:22](=[O:23])[CH2:21][C:17]1[S:16][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 15895692Methyl 2-amino-4-chloro-5-nitrobenzoate

Product 1

HCID 54055967Methyl 4-chloro-5-nitro-2-(2-(thiophen-2-yl)acetamido)benzoateYield 67.6%

Procedure

To a suspension of 2-amino-4-chloro-5-nitrobenzoic acid methyl ester (221 mg in 2.5 mL of dry 1,2-dichloroethane) was added a solution of thiophen-2-yl-acetyl chloride (169 mg in 3.0 mL dry 1,2-dichloroethane) and the mixture heated at reflux on an oil bath. After 18 hours, the reaction was cooled and the solvent removed in vacuo. Recrystallization of the crude product from methanol gave the title compound (230 mg).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux on an oil bath
  3. temperaturethe reaction was cooled
  4. customthe solvent removed in vacuo
  5. customRecrystallization of the crude product from methanol

Sources & evidence

ORD record
ord-3360fadb200f44918fa5a528d8f1207f
Source dataset
uspto-grants-2000_11
Patent number
US06150522

Reaction notes

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