Aluminium lithium hydride → (3,5-Dimethyl-1,2-thiazol-4-yl)methanol

HRID 2398397Notes

Reaction equation

HRID 2398397 reaction equation
[CH3:1][C:2]1[C:6]([C:7](O)=[O:8])=[C:5]([CH3:10])[S:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:8][CH2:7][C:6]1[C:2]([CH3:1])=[N:3][S:4][C:5]=1[CH3:10]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23361810Dimethyl-1,2-thiazole-4-carboxylic acid

Product 1

HCID 13842752(3,5-Dimethyl-1,2-thiazol-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-Dimethyl-4-isothiazolecarboxylic acid is converted to the methyl ester and the ester is reduced with lithium aluminium hydride in tetrahydrofuran to give 4-hydroxymethyl-3,5-dimethylisothiazole. Treating this hydroxymethyl compound with thionyl bromide gives 4-bromomethyl-3,5-dimethylisothiazole which is used as the starting material in the procedure of Example 121 to give N-cyano-N'-methyl-N"-[2-((3,5-dimethyl-4-isothiazolyl)methylthio)ethyl]guanidine.

Sources & evidence

ORD record
ord-dfb98566649c45b5802d358c0c8c78f6
Source dataset
uspto-grants-1977_05
Patent number
US04024271

Reaction notes

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