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

HRID 48401Notes

Reaction equation

HRID 48401 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-b962bac5c83f4c6ab72b532f520cdbab
Source dataset
uspto-grants-2004_03
Patent number
US06703421B1

Reaction notes

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