Acetic Anhydride → Methyl 3-(formylamino)-2-thiophenecarboxylate

HRID 1181279Notes

Reaction equation

HRID 1181279 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[CH3:8][O:9][C:10]([C:12]1[S:13][CH:14]=[CH:15][C:16]=1[NH2:17])=[O:11]>C(O)=O>[CH3:8][O:9][C:10]([C:12]1[S:13][CH:14]=[CH:15][C:16]=1[NH:17][CH:1]=[O:3])=[O:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 2777636Methyl 3-(formylamino)-2-thiophenecarboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Formic acid (40 mL) was added to acetic anhydride (60 mL) while cooling in an ice bath. Solid 3-amino-2-thiophenecarboxylic acid methyl ester (77, 10.3 g, 66 mmol) 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)-2-thiophenecarboxylic acid methyl ester (10.3 g, 85% 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-490b747be110418d9e46789a51c661f6
Source dataset
uspto-grants-2007_10
Patent number
US07285556B2

Reaction notes

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