Acetic Anhydride → Methyl 3-formamido-4-methylthiophene-2-carboxylate

HRID 2211431Notes

Reaction equation

HRID 2211431 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[CH3:8][O:9][C:10]([C:12]1[S:13][C:14](C)=[C:15]([CH3:18])[C:16]=1[NH2:17])=[O:11]>C(O)=O>[CH3:8][O:9][C:10]([C:12]1[S:13][CH:14]=[C:15]([CH3:18])[C:16]=1[NH:17][CH:1]=[O:3])=[O:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 4115498Methyl 3-amino-4,5-dimethylthiophene-2-carboxylate

Product 1

HCID 2777642Methyl 3-formamido-4-methylthiophene-2-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Formic acid (53 mL) was added to acetic anhydride (53 mL) while cooling in an ice bath. Solid methyl 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester (1, 18.2 g, 0.11 mol) was added to the cold solution in small portions. The cooling bath was removed and the resulting suspension was stirred at room temperature for 4 hours. The reaction mixture was diluted with water (100 mL) and the solid product collected by vacuum filtration to yield 3-(formylamino)-4-methyl-2-thiophenecarboxylic acid methyl ester (20.2 g, 95% yield) as a white solid.

Workup

  1. temperaturewhile cooling in an ice bath
  2. customThe cooling bath was removed
  3. additionThe reaction mixture was diluted with water (100 mL)
  4. filtrationthe solid product collected by vacuum filtration

Sources & evidence

ORD record
ord-cf0ed24154e14f5f9a947583dc6bd10b
Source dataset
uspto-grants-2006_09
Patent number
USRE039267E1

Reaction notes

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