Pyridine → methyl 2-(acetylamino)-5-chloro-3-thiophenecarboxylate

HRID 1605966Notes

Reaction equation

HRID 1605966 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:3])[CH3:2].C(Cl)(Cl)[Cl:15].N1C=CC=CC=1.ClCl>C(Cl)(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[S:6][C:7]([Cl:15])=[CH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 24526ChlorineHCID 2808565Methyl 2-acetamidothiophene-3-carboxylate

Product 1

HCID 818981methyl 2-(acetylamino)-5-chloro-3-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 4 parts of methyl 2-acetamidothiophene-3 -carboxylate in a mixture of 80 parts by volume of chloroform and 12 parts by volume of pyridine, 20 parts by volume of a 10 % (W/V) solution of chlorine in carbon tetrachloride is added dropwise. After stirring for further 30 minutes, the mixture is washed with an aqueous sodium bicarbonate solution and, then, with water. Evaporation of the solvent, and recrystallization of the residue from methanol gives methyl 2-acetamido-5-chlorothiophene-3-carboxylate as crystals. Colorless needles, melting point: 110°-110.5°C.

Workup

  1. additionis added dropwise
  2. washthe mixture is washed with an aqueous sodium bicarbonate solution
  3. customEvaporation of the solvent, and recrystallization of the residue from methanol

Sources & evidence

ORD record
ord-d01d152cd831486284405324321464df
Source dataset
uspto-grants-1976_04
Patent number
US03951989

Reaction notes

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