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 5243

反応式

HRID 5243 の反応式
[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]

参加物

5

反応物 3

HCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 178418641HCID 178418641、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of methyl 2-butyl-1-[[2'-(acetoxycarbamimidoyl)biphenyl-4yl)methyl]benzimidazole-7-carboxylate (2.0 g) and CS2 (1.5 g) in DMF (12 ml) gas 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 chloroformmethanol to afford pale yellow prisms (0.64 g, 32 %). m.p. 180°-181° C.

後処理

  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 chloroformmethanol

出典と根拠

ORDレコード
ord-9265263c0e12469ebf21fb271fd6edfd
出典データセット
uspto-grants-1993_09
特許番号
US05243054

関連ノート

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