Methyl 4-cyanobenzoate → HCID 15896059, compound

HRID 2289592Notes

Reaction equation

HRID 2289592 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:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1)#N>ClCCl>[CH3:27][O:26][C:24]([C:23]1[CH:28]=[CH:29][C:20]([C:12]2[N:11]3[C:7](=[N:8][C:9]4[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=43)[S:6][N:5]=2)=[CH:21][CH:22]=1)=[O:25]

Participants

4

Reactant 2

HCID 70791Methyl 4-cyanobenzoateHCID 13034031HCID 13034031, compound

Product 1

HCID 15896059HCID 15896059, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-butyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one (0.3 g, 1.2 mmole) and methyl 4-cyanobenzoate (0.41 g, 2.5 mmole) in 7 mL of dichloromethane was heated to reflux for 20 h. The precipitate was filtered and washed with dichloromethane to give 0.16 g (48%) of 3-[4-(methoxycarbonyl)phenyl]-1,2,4-thiadiazolo [4,5-a]benzimidazole as a white solid: mp 204-206° C.; 1H NMR (CDCl3) δ 8.33 (d, 2H), 7.98 (d, 2H), 7.83 (d, 1H), 7.49 (m, 2H), 7.20 (t, 1H), 4.02 (s, 3H) ppm; 13C NMR (CDCl3) δ165.96, 165.30, 151.08, 149.10, 133.16, 132.55, 130.24(2C), 128.69(3C), 125.34, 121.58, 119.96, 112.01, 52.56 ppm; IR (KBr) ν 1729, 1508, 1448, 1275, 733 cm-1 ; HRMS calcd for C16H11N3O2S, 309.0572 found 309.05719.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 h
  3. filtrationThe precipitate was filtered
  4. washwashed with dichloromethane

Sources & evidence

ORD record
ord-2180f270671c439e9f7a984a69d26621
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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