Hydrochloric Acid → 2-Thiazolecarboxylic acid, 4-(1-methylethyl)-

HRID 1815713Notes

Reaction equation

HRID 1815713 reaction equation
C([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=1)=[O:5])C.[Li+].[OH-].Cl>C1COCC1.CO.O>[CH:11]([C:9]1[N:10]=[C:6]([C:4]([OH:5])=[O:3])[S:7][CH:8]=1)([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 10821861Ethyl 4-isopropylthiazole-2-carboxylate

Product 1

HCID 224993072-Thiazolecarboxylic acid, 4-(1-methylethyl)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 3.12 g (15.7 mmol) of 4-isopropylthiazole-2-carboxylic acid ethyl ester in 32 mL of 75% THF/MeOH, was added 110 mg (31.3 mmol) of LiOH in 8 mL of H2O. The mixture was stirred overnite, the solution adjusted to pH 5 using 1N aqueous HCl solution and concentrated in vacuo to afford 4-isopropylthiazole-2-carboxylic acid as a white solid (2.97 g including salts) which was used directly in Step E: 1H NMR (500 methanol-d4) δ ppm 1.29 (d, J=6.7 Hz, 6H), 3.20 (m, 1H), 7.39 (m, 1H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-174a31fdd8cb4aac8c932f423f39e060
Source dataset
uspto-grants-2005_04
Patent number
US06878722B2

Reaction notes

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