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

HRID 2088651Notes

Reaction equation

HRID 2088651 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].C(=O)(O)[O-].[Na+]>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

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 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 were dissolved in 200 ml of dichloromethane, and 11.97 g (34.7 mmol) of 3-chloroperbenzoic acid were added. The mixture was stirred at RT for 30 min, 6 ml of DMSO and then saturated aqueous sodium bicarbonate solution were then added and the mixture was extracted three times with dichloromethane. The organic phase was dried over magnesium sulfate giving, after removal of the solvent, 2.22 g (46% of theory) of the product as an oil which was used without further purifications.

Workup

  1. extractionthe mixture was extracted three times with dichloromethane
  2. dry with materialThe organic phase was dried over magnesium sulfate giving
  3. customafter removal of the solvent, 2.22 g (46% of theory) of the product as an oil which

Sources & evidence

ORD record
ord-a168e1cdaa664e8bb7a00b659b8dd097
Source dataset
uspto-grants-2013_05
Patent number
US08436003B2

Reaction notes

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