Pyrazinecarbonitrile → HCID 23303072, compound

HRID 1953159Notes

Reaction equation

HRID 1953159 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:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1C#N>ClCCl>[N:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=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 73172PyrazinecarbonitrileHCID 13034031HCID 13034031, compound

Product 1

HCID 23303072HCID 23303072, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-butyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one (300 mg, 1.213 mmol) and pyrazinecarbonitrile (319 mg, 3.03 mmol) in 8 mL of dicloromethane was stirred at room temperature for 36 hr. The precipitate was filtered and washed with dichloromethane to give 0.28 g (91%) of 3-(2-pyrazinyl)-1,2,4-thiadiazolo[4,5-a]benzimidazole as a white solid; 1H NMR (CDCl3)δ 7.32 (t, 1H, ArH), 7.50 (t, 1H, ArH), 7.83 (d, 1H, ArH), 8.67 (d, 1H, ArH), 8.87 (br.d, 2H, py-H), 9.59 (s, 1H, py-H); mp 255-256.5° C.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with dichloromethane

Sources & evidence

ORD record
ord-945bd400973542cdb740c1bc8a7fb7c2
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

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