1-Chloro-4-(chloromethyl)benzene → 1-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine

HRID 37443

반응식

HRID 37443 반응식
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.C(NC(C)C)(C)C.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[NH2:11])=[CH:22][CH:21]=1

참가 물질

6

반응물 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 7912DiisopropylamineHCID 27239044-Methoxyphenylhydrazine hydrochloride

생성물 1

HCID 149805641-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine수율 72%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6344Dichloromethane용매

실험 절차

To a suspension of 4-methoxyphenylhydrazine hydrochloride (41 g, 230 mmol) in methylene chloride (1000 ml) under nitrogen were added diisopropylamine (79.8 g, 612 mmol), 4-chlorobenzylchloride (40.25 g, 250 mmol) and tetrabutylammonium bromide (22.8 g, 70 mmol). The resulting mixture was stirred at ambient temperature for 48 hours. The reaction mixture was then washed with water, and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 2.5% methanol in methylene chloride) followed by washing of the solid with 10% ethyl ether in hexane and drying in vacuo to provide 43.5 g of 1-(4-chlorobenzyl)-1-(4methoxyphenyl)hydrazine, mp. 55° C.

후처리

  1. washThe reaction mixture was then washed with water, and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, 2.5% methanol in methylene chloride)
  6. washby washing of the solid with 10% ethyl ether in hexane
  7. customdrying in vacuo

출처 및 근거

ORD 기록
ord-d8ce271105e24509955cfcff1c341e5f
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420282

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