2-Benzyl-1,3-thiazole-4-carboxylic acid → (2-Benzylthiazol-4-yl)methanol

HRID 27536Notes

Reaction equation

HRID 27536 reaction equation
[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([C:13](O)=[O:14])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([CH2:13][OH:14])[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14915702-Benzyl-1,3-thiazole-4-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 13102618(2-Benzylthiazol-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Benzyl-4-thiazolecarboxylic acid is converted to the methyl ester and the ester is reduced with lithium aluminium hydride in tetrahydrofuran to give 2-benzyl-4-hydroxymethylthiazole. By the procedure of Example 1 this compound is converted to 4-[(2-aminoethyl)thiomethyl]-2-benzylthiazole. Using this compound as the starting material in the procedure of Example 110 gives N-[2-((2-benzyl-4-thiazolyl)methylthio)ethyl]-N'-cyano-N"-methylguanidine.

Sources & evidence

ORD record
ord-33909fa366564c04ac1848177f0a0c25
Source dataset
uspto-grants-1980_09
Patent number
US04221802

Reaction notes

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