p-Toluenesulphonyl cyanide → 3-(3-Chlorobenzyl)-5-[(4-methylphenyl)sulphonyl]-1,2,4-thiadiazole

HRID 389830Notes

Reaction equation

HRID 389830 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][C:6]1OC(=O)[S:8][N:7]=1.[S:15]([C:25]#[N:26])([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16]>ClC1C=CC=CC=1Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][C:6]1[N:26]=[C:25]([S:15]([C:18]2[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[S:8][N:7]=1

Participants

4

Reactant 2

HCID 87946p-Toluenesulphonyl cyanideHCID 670798575-(3-Chlorobenzyl)-1,3,4-oxathiazol-2-one

Product 1

HCID 670808063-(3-Chlorobenzyl)-5-[(4-methylphenyl)sulphonyl]-1,2,4-thiadiazoleYield 58.4%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

13.00 g (52.6 mmol) of 5-(3-chlorobenzyl)-1,3,4-oxathiazol-2-one and 10.50 g (55.2 mmol) of tosyl cyanide are stirred in 15 ml of 1,2-dichlorobenzene at 160° C. for 1 h. Subsequently, the reaction mixture is cooled and purified by column chromatography. 11.2 g of product are obtained (93.3% purity, 54.5% yield).

Workup

  1. temperatureSubsequently, the reaction mixture is cooled
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-b7969cd2bf484f39afe89a79ac3652aa
Source dataset
uspto-grants-2013_02
Patent number
US08383139B2

Reaction notes

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