4-Toluenesulfonyl chloride → 2-Guanidino-4-(4-toluenesulfonyloxymethyl)thiazole

HRID 2412458Notes

Reaction equation

HRID 2412458 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].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][O:11][S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=2)(=[O:20])=[O:19])[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 178512688HCID 178512688, compound

Product 1

HCID 1784277022-Guanidino-4-(4-toluenesulfonyloxymethyl)thiazoleYield 45.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-guanidino-4-hydroxymethylthiazole (0.69 g) in pyridine (5 ml) is gradually added 4-toluenesulfonyl chloride (0.763 g), and the resultant mixture is stirred at room temperature for 4 hours. The resultant mixture is concentrated in vacuum, and the residue is chromatographed on a column of silica gel, which is eluted with methanol. The eluate is concentrated in vacuum to give 2-guanidino-4-(4-toluenesulfonyloxymethyl)thiazole (0.6 g) as an oil. The yield is 45.8%.

Workup

  1. concentrationThe resultant mixture is concentrated in vacuum
  2. customthe residue 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-f465af9198044f95b59494dca3f0287d
Source dataset
uspto-grants-1985_01
Patent number
US04492794

Reaction notes

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