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

HRID 374062

Reaktionsgleichung

Reaktionsgleichung von HRID 374062
[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) δ8.14-8.00(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-d021ca009b6c4322970f5f0d9c4fb375
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166214

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