Triphenylphosphine → [4-(Cyclopropanecarbonylaminocarbonyl)butyl]triphenylphosphonium bromide

HRID 1075843

Reaktionsgleichung

Reaktionsgleichung von HRID 1075843
[CH:1]1([C:4]([NH:6][C:7](=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11][Br:12])=[O:5])[CH2:3][CH2:2]1.[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[Br-:12].[CH:1]1([C:4]([NH:6][C:7]([CH2:8][CH2:9][CH2:10][CH2:11][P+:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[O:5])[CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 21540959N-cyclopropanecarbonyl-5-bromovaleramide

Produkt 1

HCID 21540964[4-(Cyclopropanecarbonylaminocarbonyl)butyl]triphenylphosphonium bromideAusbeute 23,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 4.96 g. (20 mmoles) of the N-cyclopropanecarbonyl-5-bromovaleramide prepared above, 7.86 g. (30 mmoles) of triphenylphosphine, and 50 ml. of acetonitrile were heated at reflux temperatures under nitrogen for 112 hours. The mixture was then concentrated and the resultant white foam was purified by column chromatography on Silica gel (Baker 60-200 mesh) using 5% methanol in methylene chloride as eluent. After removal of starting materials and less polar impurities, the desired [4-(cyclopropanecarbonylaminocarbonyl)butyl]triphenylphosphonium bromide was obtained as a white hygroscopic foam weighing 2.42 g. (23.8% yield).

Aufarbeitung

  1. additionA mixture of 4.96 g
  2. temperatureat reflux temperatures under nitrogen for 112 hours
  3. concentrationThe mixture was then concentrated
  4. customthe resultant white foam was purified by column chromatography on Silica gel (Baker 60-200 mesh)
  5. customAfter removal of starting materials and less polar impurities

Quellen und Nachweise

ORD-Eintrag
ord-2605b9d00f7a4c6fbc91d8d4a3bbd40f
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03954741

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