p-Toluenesulphonyl cyanide → HCID 9927470, compound

HRID 2289593Notes

Reaction equation

HRID 2289593 reaction equation
C([N:5]1[C:12](=O)[N:11]2[C:7](=[N:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=32)[S:6]1)CCC.[C:18]1([CH3:29])[CH:23]=[CH:22][C:21]([S:24](C#N)(=[O:26])=[O:25])=[CH:20][CH:19]=1>ClCCl>[CH3:29][C:18]1[CH:23]=[CH:22][C:21]([S:24]([C:12]2[N:11]3[C:7](=[N:8][C:9]4[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=43)[S:6][N:5]=2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 87946p-Toluenesulphonyl cyanideHCID 13034031HCID 13034031, compound

Product 1

HCID 9927470HCID 9927470, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-butyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one (10.0 g, 40.4 mmole) and p-toluenesulfonyl cyanide (14.7 g, 81.0 mmole) in 120 mL of dichloromethane was stirred at room temperature for 20 h. The precipitate was filtered and washed with dichloromethane to yield 12.2 g (91%) of 3-(4-methylphenyl-sulfonyl)-1,2,4-thiadiazolo[4,5-a]benzimidazole as white powder: mp 231-234 ° C.; 1H NMR (CDCl3) δ 8.53 (d, 1H), 8.04 (d, 2H), 7.82 (d, 1H), 7.56-7.44 (m, 4H), 2.53 (s, 3H) ppm; 13C NMR (CDCl3) δ 163.72, 150.38, 147.97, 147.54, 132.48, 130.30(2C), 129.97(2C), 128.49, 126.14, 123.06, 119.70, 114.67, 21.93 ppm; IR (KBr) ν 1592, 1525, 1444, 1337, 1151, 1081, 735 cm-1 ; HRMS calcd for C15H11N3O2S2 : 329.0293, found: 329.0300. Anal. Calcd for C15H11N3O2S2 : C, 54.70; H, 3.37; N, 12.76. Found: C, 54.29; H, 3.14; N, 14.59.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with dichloromethane

Sources & evidence

ORD record
ord-b24d31dc4e5544e898f5f837db291775
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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