Methyl iodide → 2-(4-Methoxyphenyl)-1-methyl-1H-benzimidazole-4-carboxamide

HRID 382355ノート

反応式

HRID 382355 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]3[C:17]([C:18]([NH2:20])=[O:19])=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.[OH-].[K+].[CH3:23]I>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([CH3:23])[C:12]3[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([NH2:20])=[O:19])[C:11]=3[N:10]=2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178488846HCID 178488846、化合物

生成物 1

HCID 105407722-(4-Methoxyphenyl)-1-methyl-1H-benzimidazole-4-carboxamide

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

2-(4′-Methoxyphenyl)benzimidazole-4-carboxamide (NU1076 from Example 5) (105.3 mg, 0.394 mmol) and powdered potassium hydroxide (22 mg, 0.394 mmol) were suspended in acetone (4 ml) and stirred until all the solids had dissolved. Methyl iodide (24.6 μll, 0.394 mmol) was added and the reaction stirred at room temperature overnight. The solvent was removed under reduced pressure and the white solid residue purified by column chromatography with dichloromethane/methanol 95:5 to give fine white crystals of the title compound. (33.2 mg, 30%) mp 289-292° C.; Found C 68.62 H 5.36 N 14.67 C16Hl5N3O2 Requires C 68.33 H 5.34 N 14.95; vmax(cm−1) 3309.23, 3141.44, 1671.29, 1605.30, 1255.08, δH 3.95 (3H, s), 4.02 (3H, s), 7.22-7.27 (2H, d), 7.44-7.52 (1H, t), 7.86-8.00 (5H, m), 9.4 (1H, br s, NH); m/z (EI) 281 (M+), 264, 250.

後処理

  1. dissolutionhad dissolved
  2. stirringthe reaction stirred at room temperature overnight
  3. customThe solvent was removed under reduced pressure
  4. customthe white solid residue purified by column chromatography with dichloromethane/methanol 95:5

出典と根拠

ORDレコード
ord-056a59c1f9a940fd87e11548b35443a8
出典データセット
uspto-grants-2001_10
特許番号
US06310082B1

反応ノート

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