Acetic Anhydride → 2-Formylaminothiophene-3-carboxylic acid ethyl ester

HRID 1581966Notes

Reaction equation

HRID 1581966 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[CH2:8]([O:10][C:11]([C:13]1[CH:17]=[CH:16][S:15][C:14]=1[NH2:18])=[O:12])[CH3:9]>C(O)=O>[CH2:8]([O:10][C:11]([C:13]1[CH:17]=[CH:16][S:15][C:14]=1[NH:18][CH:1]=[O:3])=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1988156Ethyl 2-aminothiophene-3-carboxylate

Product 1

HCID 186182032-Formylaminothiophene-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To acetic anhydride (4.7 ml) under ice cooling, formic acid (4.7 ml) was added dropwise, to which 2-aminothiophene-3-carboxylic acid ethyl ester (2.8 g, 16.4 mmol) was added and stirred at room temperature for 2 hours. After the solvent was distilled off under reduced pressure, ether was added, and the precipitate that deposited was filtered off. Ether was distilled off under reduced pressure to obtain 2-formylaminothiophene-3-carboxylic acid ethyl ester (3.0 g, 15.3 mmol).

Workup

  1. additionwas added
  2. distillationAfter the solvent was distilled off under reduced pressure, ether
  3. additionwas added
  4. filtrationthe precipitate that deposited was filtered off
  5. distillationEther was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3f25ee6925674d2e93cb764d371807d7
Source dataset
uspto-grants-2004_05
Patent number
US06734180B1

Reaction notes

Loading…