Ammonium Hydroxide → 2-Amino-1,3-thiazole-4-carboxamide

HRID 2222990Notes

Reaction equation

HRID 2222990 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([NH2:11])[S:9][CH:10]=1)=O)C.[OH-].[NH4+:13]>>[NH2:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([NH2:13])=[O:3])[N:7]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 73216Ethyl 2-aminothiazole-4-carboxylate

Product 1

HCID 2571492-Amino-1,3-thiazole-4-carboxamideYield 69%

Procedure

A solution of 2-amino-thiazole-4-carboxylic acid ethyl ester (258 mg, 1.5 mmol) (prepared as described in example 3, step 1) in concentrated aqueous ammonium hydroxide was heated to reflux for 8 hours. The reaction mixture was concentrated to dryness and residual water removed by azeotropic distillation with toluene. The residue was purified by chromatography over silica gel eluted with 2% v/v methanol in ethyl acetate to give 2-amino-thiazole-4-carboxylic acid amide as a colorless solid (149 mg, 69%).

Workup

  1. temperatureto reflux for 8 hours
  2. concentrationThe reaction mixture was concentrated to dryness and residual water
  3. customremoved by azeotropic distillation with toluene
  4. customThe residue was purified by chromatography over silica gel
  5. washeluted with 2% v/v methanol in ethyl acetate

Sources & evidence

ORD record
ord-38053d008abb47bf8ad6a70a5958a376
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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