Dimethyl Sulfoxide → 5-Thiazolecarbonitrile, 4-amino-2-(methylsulfonyl)-

HRID 2389746Notes

Reaction equation

HRID 2389746 reaction equation
[NH2:1][C:2]1[N:3]=C(SC)[S:5][C:6]=1[C:7]#[N:8].ClC1C=CC=C(C(OO)=[O:19])C=1.[CH3:22][S:23]([CH3:25])=[O:24]>ClCCl>[NH2:1][C:2]1[N:3]=[C:22]([S:23]([CH3:25])(=[O:19])=[O:24])[S:5][C:6]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 70297m-Chloroperbenzoic acidHCID 6764114-Amino-2-(methylsulfanyl)-1,3-thiazole-5-carbonitrile

Product 1

HCID 198350775-Thiazolecarbonitrile, 4-amino-2-(methylsulfonyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.7 g (15.77 mmol) of 4-amino-2-(methylthio)-1,3-thiazole-5-carbonitrile are dissolved in 200 ml of dichloromethane, and 11.97 g (34.7 mmol) of 3-chloroperbenzoic acid are added. The mixture is stirred at RT for 30 min and then 6 ml of DMSO are added, and then saturated aqueous sodium bicarbonate solution, and the mixture is extracted three times with dichloromethane. Drying of the organic phase over magnesium sulphate and removal of the solvent result in 2.22 g (46% of theory) of the product as an oil, which is employed without further purification.

Workup

  1. extractionsaturated aqueous sodium bicarbonate solution, and the mixture is extracted three times with dichloromethane
  2. dry with materialDrying of the organic phase over magnesium sulphate and removal of the solvent

Sources & evidence

ORD record
ord-5ca75412ddeb4c7abe5ac2c3f711bbde
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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