Lithium hydroxide, monohydrate → 3-Acetyl-1,2-thiazole-4-carboxylic acid

HRID 2372197Notes

Reaction equation

HRID 2372197 reaction equation
C(=O)(O)[O-].[Na+].[C:6]([C:9]1[C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][S:11][N:10]=1)(=[O:8])[CH3:7].O.[OH-].[Li+]>CS(C)=O>[C:6]([C:9]1[C:13]([C:14]([OH:16])=[O:15])=[CH:12][S:11][N:10]=1)(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 516892Sodium BicarbonateHCID 19902851HCID 19902851, compound

Product 1

HCID 229086823-Acetyl-1,2-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following generally the procedure of Example 28, ethyl 3-ethyl-4-isothiazolecarboxylate is reacted with NBS and benzoyl peroxide to give ethyl 3-(1-bromoethyl)-4-isothiazolecarboxylate, which is then reacted with sodium bicarbonate and DMSO and the resulting ethyl 3-acetyl-4-isothiazolecarboxylate is treated with lithium hydroxide monohydrate to yield 3-acetyl-4-isothiazolecarboxylic acid.

Sources & evidence

ORD record
ord-537d71ea7459410b8f428ed69d8a85be
Source dataset
uspto-grants-1992_03
Patent number
US05098462

Reaction notes

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