Sodium Hydroxide → 2-Amino-4-methyl-thiazole-5-carboxylic acid

HRID 883130Notes

Reaction equation

HRID 883130 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10]CC)=[O:9])=[C:5]([CH3:7])[N:6]=1.[OH-].[Na+]>O1CCCC1.O>[NH2:1][C:2]1[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

Product 1

HCID 8322432-Amino-4-methyl-thiazole-5-carboxylic acidYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 2-amino-4-methylthiazole-5-carboxylate (6.58 g, 35.5 mmol) and NaOH (5.40 g, 135.0 mmol) in tetrahydrofuran (60 mL) and water (30 mL) was heated to reflux overnight. Tetrahydrofuran was removed in vacuo, and the residue was neutralized with 5% hydrochloric acid solution to pH 56. The precipitate obtained was collected by filtration and dried to afford the crude 2-amino-4-methylthiazole-5-carboxylic acid (5.20 g, 94%): 1H NMR (300 MHz, DMSO-d6) δ 7.63 (s, 2H), 2.30 (s, 3H); MS (ES+) m/z 159.1 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customTetrahydrofuran was removed in vacuo
  4. customThe precipitate obtained
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-ebe1f71f991a4d8a8702f5738dc56fee
Source dataset
uspto-grants-2012_08
Patent number
US08236835B2

Reaction notes

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