Phenylglyoxylonitrile → HCID 9838563, compound

HRID 2289590Notes

Reaction equation

HRID 2289590 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](C#N)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[O:25]=[C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH: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 11953PhenylglyoxylonitrileHCID 13034031HCID 13034031, compound

Product 1

HCID 9838563HCID 9838563, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-butyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one (6.0 g, 24.3 mmole) and benzoyl cyanide (6.36 g, 48.5 mmole) in 80 mL of dichloromethane was stirred at room temperature for 24 h. The precipitate was filtered and washed with dichloromethane. The crude product was recrystallized from acetone to give 6.48 g (96%) of 3-(oxophenylmethyl)-1,2,4-thiadiazolo[4,5-a]benzimidazole as yellow crystals: mp 190-191° C.; 1H NMR (CDCl3) δ 8.35 (d, 3H), 7.82 (d, 1H), 7.73 (t, 1H), 7.59 (t, 2H), 7.50 (t, 1H), 7.36 (t, 1H) ppm; 13C NMR (CDCl3) δ180.86, 163.69, 150.82, 146.70, 134.79, 134.34, 131.22 (2C), 129.46 (2C), 128.74, 125.82, 122.27, 119.49, 115.23 ppm; IR (KBr) ν 1671 cm-1 ; HRMS calcd for C15H9N3OS: 279.0466, found: 279.0475. Anal. Calcd for C15H9N3OS: C, 64.50; H, 3.25; N, 15.04. Found: C, 63.93; H, 3.10; N, 14.53.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with dichloromethane
  3. customThe crude product was recrystallized from acetone

Sources & evidence

ORD record
ord-483d3e924274455fb82a9b49b94fc126
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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