Carbonocyanidic acid, methyl ester → HCID 15888354, compound

HRID 1488991Notes

Reaction equation

HRID 1488991 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) δ8.61 (d, 1H), 7.82 (d, 1H), 7.51 (t, 1H), 7.31 (t, 1H), 4.17 (s, 3H) ppm; 13C NMR (CDCl3) δ164.02, 156.51, 150.67, 140.89, 129.34, 125.93, 122.41, 119.48, 115.41, 54.04 ppm; IR (KBr) ν1733 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-25c83146ee61431daf00995cd90ddf3c
Source dataset
uspto-grants-1997_10
Patent number
US05677302

Reaction notes

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