Methanesulfonyl chloride → 2-Guanidino-4-(methanesulfonyloxymethyl)thiazole

HRID 2412459Notes

Reaction equation

HRID 2412459 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

HCID 31297Methanesulfonyl chlorideHCID 178512688HCID 178512688, compound

Product 1

HCID 1785052772-Guanidino-4-(methanesulfonyloxymethyl)thiazoleYield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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%.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuum
  2. customthe residual oil is chromatographed on a column of silica gel, which
  3. washis eluted with methanol
  4. concentrationThe eluate is concentrated in vacuum

Sources & evidence

ORD record
ord-306843c60df84c56a8d782f69ef0f2b1
Source dataset
uspto-grants-1985_01
Patent number
US04492794

Reaction notes

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