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

HRID 2067330Notes

Reaction equation

HRID 2067330 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 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethyl 2-amino-4-methylthiazole-5-carboxylate (6.58 g, 35.00 mmol) and sodium hydroxide (5.40 g, 135.00 mmol) in the mixture of tetrahydrofuran (60 mL) and water (30 mL) was heated at reflux for 18 hours. The tetrahydrofuran was removed in vacuo, and the aqueous solution was neutralized with 5% HCl solution to pH 5-6. The precipitated solid was collected by filtration, washed with water and dried to afford 2-amino-4-methylthiazole-5-carboxylic acid as a white solid in 94% yield (5.20 g): 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. temperatureat reflux for 18 hours
  3. customThe tetrahydrofuran was removed in vacuo
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-8173cb9d66cd4f9085c338f1efedda2d
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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