Ammonium Hydroxide → 2-(Thiophen-3-yl)acetamide

HRID 1366651Notes

Reaction equation

HRID 1366651 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([OH:9])=O)=[CH:2]1.C(Cl)(=O)C(Cl)=O.[OH-].[NH4+:17]>C(Cl)Cl>[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([NH2:17])=[O:9])=[CH:2]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 234043-Thiophenacetic acidHCID 65578Oxalyl chloride

Product 1

HCID 5663352-(Thiophen-3-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Commercially available 3-thiophene acetic acid (2.0 g, 14.07 mmol) was dissolved in DCM (45 mL) under nitrogen. Then oxalyl chloride (1.35 mL, 15.48 mmol) was added and the reaction was stirred overnight. Then ammonium hydroxide (30% as NH3 solution) (8.22 mL) was added dropwise with stirring. The reaction mixture was evaporated to provide 2-(3-thienyl)acetamide as a beige solid (3.2082 g). LCMS: (M+H)+=142.1.

Workup

  1. stirringwith stirring
  2. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-8581ebca557246469fd4a6477041e9dd
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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