Tetrahydrofuran → 2-Amino-4-methyl-thiazole-5-carboxylic acid

HRID 2381782Notes

Reaction equation

HRID 2381782 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.O1CCCC1.[OH-].[Na+]>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 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

Product 1

HCID 8322432-Amino-4-methyl-thiazole-5-carboxylic acidYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 2-amino-4-methylthiazole-5-carboxylate (2.19 g, 11.8 mmol) in a 1:1 mixture of tetrahydrofuran (20 mL) and water (10 mL) was added sodium hydroxide (1.80 g, 45.0 mmol). The reaction mixture was refluxed for 18 hours and allowed to cool down to ambient temperature. The organic solvent was removed in vacuo. The aqueous solution was acidified with 10% aqueous hydrochloric acid solution. The colorless solid was collected and dried to afford 2-amino-4-methylthiazole-5-carboxylic acid (1.40 g, 75%): 1H NMR (300 MHz, DMSO-d6) δ 11.95 (s, 1H), 7.26 (s, 2H), 2.01 (s, 3H); MS (ES+) m/z 159.3 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. customThe organic solvent was removed in vacuo
  3. customThe colorless solid was collected
  4. customdried

Sources & evidence

ORD record
ord-273ae195ebff4ba885c8606562b57957
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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