Hydrochloric Acid → 4-tert-Butyl-1,3-thiazole-2-carboxylic acid

HRID 1374255Notes

Reaction equation

HRID 1374255 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]([O:12]CC)=[O:11])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([C:5]1[N:6]=[C:7]([C:10]([OH:12])=[O:11])[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21075145HCID 21075145, compound

Product 1

HCID 197863434-tert-Butyl-1,3-thiazole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl thiooxamate (0.75 g, 5.6 mol) and 1-bromopinacolone (1.0 g, 5.6 mol) in ethanol was heated to reflux for 2 h. The solvent was removed in vacuo and the residue dissolved in CH2Cl2 and washed with water and brine, concentrated and the residue chromatographed on silica gel (10% Ethyl acetate/hexane) to give 0.8 g of ethyl 4-tert-butylthiazole-2-carboxylate as an oil. The ester was dissolved in methanol (5 ml) and treated with 1N NaOH (30 ml) and stirred overnight at room temperature. The solution was acidified with 1N HCl and extracted into CH2Cl2 and washed with water. The solvent was removed under vacuum to give 0.55 g of 4-tert-butylthiazole-2-carboxylic acid as a off-white solid. MS found: (M+H)+=186.24

Workup

  1. extractionextracted into CH2Cl2
  2. washwashed with water
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-27ef19853c2e430296a420c81ca619c8
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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