Cyanogen Bromide → HCID 10198942, compound

HRID 1953145Notes

Reaction equation

HRID 1953145 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.N#C[Br:20]>ClCCl>[Br:20][C:12]1[N:11]2[C:7](=[N:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=32)[S:6][N:5]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 13034031HCID 13034031, compound

Product 1

HCID 10198942HCID 10198942, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-butyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one (5.0 g, 20.2 mmole) and cyanogen bromide (4.28 g, 40.4 mmole) in 100 mL of dichloromethane was stirred at room temperature for 26 h. The precipitate was filtered and washed with dichloromethane to yield 4.18 g (81%) of 3-bromo-1,2,4-thiadiazolo[4,5-a]benzimidazole as a white powder: mp 189-190° C.; 1H NMR (CDCl3)δ 8.23 (d, 1H), 7.82 (d, 1H), 7.52 (t, 1H), 7.42 (d, 1H) ppm; 13C NMR (1:1 CDCl3 :DMSO-d6):δ 162.78, 149.67, 129.22, 125.53, 122.25, 119.48, 117.25, 111.27 ppm; IR (KBr):ν 3025, 2925, 1601, 1493, 1451, 1028, 757, 701 cm-1 ; HRMS calcd for C8H4N3SBr 252.9309, found 252.9307. Anal. Calcd for C8H4N3SBr: C, 37.81;H, 1.59; N, 16.54. Found: C, 37.44; H, 1.33; N. 16.57.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with dichloromethane

Sources & evidence

ORD record
ord-8dbd7938d05a413e8ebd1aa7263fc229
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

Loading…