Carbon Disulfide → Methyl 2-butyl-1-[[2'-(2,5-dihydro-5-thioxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazol-7-carboxylate

HRID 1418620Notes

Reaction equation

HRID 1418620 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23](=[NH:29])[NH:24][O:25][C:26](=O)C)=[CH:13][CH:12]=2)[C:8]2[C:30]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=[CH:33][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].C(=S)=[S:39].[H-].[Na+]>CN(C=O)C>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:24][O:25][C:26](=[S:39])[N:29]=3)=[CH:13][CH:12]=2)[C:8]2[C:30]([C:34]([O:36][CH3:37])=[O:35])=[CH:31][CH:32]=[CH:33][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 178418641HCID 178418641, compound

Product 1

HCID 10649000Methyl 2-butyl-1-[[2'-(2,5-dihydro-5-thioxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazol-7-carboxylateYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 2-butyl-1-[[2'-(acetoxycarbamimidoyl)biphenyl-4-yl)methyl]benzimidazole-7-carboxylate (2.0 g) and CS2 (1.5 g) in DMF (12 ml) was added sodium hydride (60% in oil, 0.56 g) during a period of 10 minutes and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice-water and the pH of the solution was adjusted to 3. The mixture was extracted with ethylacetate and the extract was washed with water, dried, and concentrated to dryness. The residue was crystallized from chloroform-methanol to afford pale yellow prisms (0.64 g, 32%).

Workup

  1. extractionThe mixture was extracted with ethylacetate
  2. washthe extract was washed with water
  3. customdried
  4. concentrationconcentrated to dryness
  5. customThe residue was crystallized from chloroform-methanol

Sources & evidence

ORD record
ord-10d298b912784bb59c5e741e30fbc7c0
Source dataset
uspto-grants-1999_03
Patent number
US05883111

Reaction notes

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