Sodium hydride → 2-Butyl 4-methyl-1-[(4-nitrophenyl)methyl]-1H-benzimidazole

HRID 5021

反応式

HRID 5021 の反応式
[H-].[Na+].[CH2:3]([C:7]1[NH:8][C:9]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:4][CH2:5][CH3:6].[N+:17]([C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1)([O-:19])=[O:18]>CN(C=O)C>[CH2:3]([C:7]1[N:11]([CH2:24][C:23]2[CH:26]=[CH:27][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=2)[C:10]2[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:9]=2[N:8]=1)[CH2:4][CH2:5][CH3:6]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 178418620HCID 178418620、化合物

生成物 1

HCID 197975362-Butyl 4-methyl-1-[(4-nitrophenyl)methyl]-1H-benzimidazole収率 87.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

To a slurry of NaH (60%, 0.21 g. 5.3 mmol) in DMF was added with stirring a solution of 2-butyl-4-methyl-benzimidazole (1 g. 5.3 mmol) in DMF (20 mL under nitrogen atmosphere. After the gas evolution was complete, the reaction mixture was cooled in ice and a solution of 4-nitrobenzyl bromide (1.5 g, 5.3 mmol) in DMF (5 mL) was added with stirring. The reaction mixture was allowed to warm up slowly to room temperature and stirred for 16 hours. DMF was distilled under reduced pressure and the residue was taken up in EtOAc, and the solution was washed with water. It was dried over MgSO4 and evaporated to give a solid which was chromatographed (CH2Cl2 /EtOAc 4/1-EtOAc) to give 1.5 g of a solid, MP 115°-116° C.

後処理

  1. temperaturethe reaction mixture was cooled in ice
  2. stirringstirred for 16 hours
  3. distillationDMF was distilled under reduced pressure
  4. washthe solution was washed with water
  5. dry with materialIt was dried over MgSO4
  6. customevaporated
  7. customto give a solid which
  8. customwas chromatographed (CH2Cl2 /EtOAc 4/1-EtOAc)

出典と根拠

ORDレコード
ord-8b03c4b147cc4e73961cfb46cd3fddcd
出典データセット
uspto-grants-1993_09
特許番号
US05242939

関連ノート

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