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

HRID 1109065

反応式

HRID 1109065 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4eca12b813304094981e480c5ef347a6
出典データセット
uspto-grants-1994_06
特許番号
US05318984

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