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

HRID 2067306Notes

Reaction equation

HRID 2067306 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 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 5˜6. 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-5425e026b1854963a8b462f29a4b6e37
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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