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

HRID 5021

반응식

HRID 5021 반응식
[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]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 178418620HCID 178418620, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8b03c4b147cc4e73961cfb46cd3fddcd
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242939

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