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

HRID 57665Notes

Reaction equation

HRID 57665 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 (15.8 mmol) of 4-amino-2-(methylsulfanyl)-1,3-thiazole-5-carbonitrile were dissolved in 500 ml of dichloromethane, and 12 g (34.7 mmol) of 50% strength 3-chloroperbenzoic acid were added. The mixture was stirred at RT for 30 min. 6 ml of DMSO were added, and the reaction mixture was washed with saturated sodium bicarbonate solution and water. The organic phase was dried over magnesium sulfate and concentrated on a rotary evaporator. This gave 2.2 g (46% of theory) of the product as a solid.

Workup

  1. washthe reaction mixture was washed with saturated sodium bicarbonate solution and water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-0b3d938f02f44a988346be405ad2d744
Source dataset
uspto-grants-2016_09
Patent number
US09434731B2

Reaction notes

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