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

HRID 560557

Reaction equation

HRID 560557 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-d4) 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-bce082bfe53c426fa638240187eb83ff
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Linked notes

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