Methanesulfonyl chloride → 2-Guanidino-4-(methanesulfonyloxymethyl)thiazole
Reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][OH:11])[N:9]=1)[C:2]([NH2:4])=[NH:3].[CH3:12][S:13](Cl)(=[O:15])=[O:14]>N1C=CC=CC=1>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][O:11][S:13]([CH3:12])(=[O:15])=[O:14])[N:9]=1)[C:2]([NH2:4])=[NH:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-guanidino-4-hydroxymethylthiazole (0.86 g) in pyridine (6 ml) is gradually added methanesulfonyl chloride (0.6 g) under ice cooling, and the resultant mixture is stirred at room temperature for 2 hours. The reaction mixture is concentrated in vacuum, and the residual oil is chromatographed on a column of silica gel, which is eluted with methanol. The eluate is concentrated in vacuum to give 2-guanidino-4-(methanesulfonyloxymethyl)thiazole (1.2 g) as an oil. The yield is 96%.