Dimethylformamide → 7-[(4-chlorophenyl)(isopropyl)amino]-3-(4-methoxybenzyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 2235554노트

반응식

HRID 2235554 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]3[N:15]([CH3:28])[C:16](=[O:27])[N:17]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.Br[CH:30]([CH3:32])[CH3:31].CN(C)C=O.[H-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:30]([CH3:32])[CH3:31])[C:9]2[C:14]3[N:15]([CH3:28])[C:16](=[O:27])[N:17]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 685810534-[(4-chlorophenyl)amino]-1-(4-methoxybenzyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one

생성물 1

HCID 685813547-[(4-chlorophenyl)(isopropyl)amino]-3-(4-methoxybenzyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one수율 62%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

To a mixture of 7-[(4-chlorophenyl)amino]-3-(4-methoxybenzyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (0.118 g, 0.30 mmol), 2-bromopropane (0.056 ml, 0.60 mmol), tetrabutylammonium iodide (small amounts) and N,N-dimethylformamide (2 ml) was added sodium hydride (16 mg, 0.60 mmol, 90% dry). The mixture was stirred at 60° C. for 6 h. The mixture was diluted with water (20 ml) and extracted with ethyl acetate (40 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was flash chromatographed with 20-33% ethyl acetate/hexanes to give 80.6 mg (62%) of the title compound as an oil.

후처리

  1. extractionextracted with ethyl acetate (40 ml)
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customchromatographed with 20-33% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-f004aa2b146e4845b0f68f75d23c8797
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07714009B2

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