Carbon tetrabromide → N-(5-bromopentyl)-N'-(2,4-difluorophenyl)-N-heptylurea

HRID 1109065

반응식

HRID 1109065 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:25])[N:11]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]O.C(Br)(Br)(Br)[Br:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:27][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:10]([NH:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])=[O:25]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11725825Urea, N'-(2,4-difluorophenyl)-N-heptyl-N-(5-hydroxypentyl)-

생성물 1

HCID 10342005N-(5-bromopentyl)-N'-(2,4-difluorophenyl)-N-heptylurea수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Part D. To a solution of N'-(2,4-difluorophenyl)-N-heptyl-N-5-hydroxypentylurea (15.0 g, 0.042 mol) and carbon tetrabromide (16.75 g, 0.051 mol) in methylene chloride (350 mL) under a nitrogen atmosphere at ambient temperature, a solution of triphenylphosphine (13.24 g, 0.051 mol) in methylene chloride (100 mL) was added slowly. The reaction mixture was stirred for 3 hours and was concentrated in vacuo to give crude viscous oil. The product was purified by flash chromatography on silica gel (400 mL) eluting with hexane:ethyl acetate (90:10 v:v) to give N-(5-bromopentyl)-N'-(2,4-difluorophenyl)-N-heptylurea as a viscous colorless oil (17.5 g, 0.042 mol). 1H NMR (CDCl3) δ 8.14-8.00(m, 1H), 6.92-6.79(m, 2H), 6.35(bs, 1H), 3.49-3.25(m, 6H), 1.99-1.26 (m, 16H), 0. 915 (t, 3H).

후처리

  1. concentrationwas concentrated in vacuo
  2. customto give crude viscous oil
  3. customThe product was purified by flash chromatography on silica gel (400 mL)
  4. washeluting with hexane:ethyl acetate (90:10 v:v)

출처 및 근거

ORD 기록
ord-4eca12b813304094981e480c5ef347a6
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05318984

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