Pyridine-2-carbonitrile → HCID 9794974, compound

HRID 2289595Notes

Reaction equation

HRID 2289595 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([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)#N>ClCCl>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[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 7522Pyridine-2-carbonitrileHCID 13034031HCID 13034031, compound

Product 1

HCID 9794974HCID 9794974, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-butyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one (15.0 g, 60.7 mmole) and 2-cyanopyridine (13.3 g, 0.13 mole) in 150 mL of dichloromethane was stirred at room temperature for 72 h. The precipitate was filtered and washed with dichloromethane to give 10.4 g (68%) of 3-(2-pyridyl)-1,2,4-thiadiazolo[4,5-a]benzimidazole as a white solid: mp 173-174° C.; 1H NMR (CDCl3) δ 8.90 (d, 1H), 8.70 (d, 1H), 8.30 (d, 1H), 7.99 (t, 1H), 7.80 (d, 1H), 7.57 (t, 1H) 7.47 (t, 1H), 7.37 (t, 1H) ppm; 13C NMR (CDCl3) δ 166.10, 151.09, 150.11, 148.74, 147.73, 137.38, 130.50, 125.85, 125.24, 124.52, 121.41, 119.11, 116.33 ppm; IR (KBr) ν 3419, 3054, 1611, 1587, 1501, 1463, 1446, 727 cm-1. HRMS calcd for C13H8N4S 252.0470, found 252.0882. Anal. Calcd for C13H8N4S: C, 61.89; H, 3.20; N, 22.21. Found: C, 61.48; H, 3.30; N, 22.24.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with dichloromethane

Sources & evidence

ORD record
ord-052b435ab96245d5b3ea0c51e9a54afb
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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