Carbonocyanidic acid, methyl ester → HCID 15888354, compound

HRID 1953142Notes

Reaction equation

HRID 1953142 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]([O:22][CH3:23])=[O:21])#N>ClCCl>[CH3:23][O:22][C: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)=[O:21]

Participants

4

Reactant 2

HCID 28660Carbonocyanidic acid, methyl esterHCID 13034031HCID 13034031, compound

Product 1

HCID 15888354HCID 15888354, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-butyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one (4.0 g, 16.2 mmole) and methyl cyanoformate (2.75 g, 32.4 mmole) in 30 mL of dichloromethane was stirred at room temperature for 21 h. The precipitate was filtered and washed with dichloromethane to give 3.36 g (84%) of 3-(methoxycarbonyl)-1,2,4-thiadiazolo [4,5-a]benzimidazole as a colourless solid: mp 208-209° C.; 1H NMR (CDCl3)δ 8.61 (d, 1H), 7.82 (d, 1H), 7.51 (t, 1H), 7.31 (t, 1H), 4.17 (s, 3H) ppm; 13C NMR (CDCl3)δ 164.02, 156.51, 150.67, 140.89, 129.34, 125.93, 122.41, 119.48, 115.41, 54.04 ppm; IR (KBr)ν 1733 cm-1 ; HRMS calcd for C10H7N3O2S 233.0259, found 233.0262. Anal. Calcd. for C10H7N3O2S: C, 51.50;H, 3.02; N, 18.02. Found: C, 51.41;H. 2.89; N, 18.16.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with dichloromethane

Sources & evidence

ORD record
ord-bc46c95b0cf445058b462d24ff83d469
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

Loading…