Acetic Anhydride → Diethyl 5-acetamido-3-methylthiophene-2,4-dicarboxylate

HRID 460971

Reaction equation

HRID 460971 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([NH2:17])=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]=1[CH3:11])=[O:5])[CH3:2].[C:18](OC(=O)C)(=[O:20])[CH3:19]>>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([NH:17][C:18](=[O:20])[CH3:19])=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 78537Diethyl 5-amino-3-methylthiophene-2,4-dicarboxylate

Product 1

HCID 291812Diethyl 5-acetamido-3-methylthiophene-2,4-dicarboxylate

Procedure

A solution of 23.0 g. (0.09 mol) of 2,4-diethoxycarbonyl-3-methyl-5-aminothiophene in 250 ml. of acetic anhydride was heated to 100° C. for 1.5 hrs. The resulting mixture was cooled in an ice bath and the precipitated crystals were filtered to yield 2,4-diethoxycarbonyl-3-methyl-5-acetylamino-thiophene, m.p. 130°-131° C.

Workup

  1. temperatureThe resulting mixture was cooled in an ice bath
  2. filtrationthe precipitated crystals were filtered

Sources & evidence

ORD record
ord-ca6932ddd2f341b8b430cbd38161b4b3
Source dataset
uspto-grants-1977_12
Patent number
US04061656

Linked notes

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