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

HRID 1109065

Reaktionsgleichung

Reaktionsgleichung von HRID 1109065
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-4eca12b813304094981e480c5ef347a6
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05318984

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