Triphenylphosphine → HCID 20488635, compound

HRID 1075841Notes

Reaction equation

HRID 1075841 reaction equation
[C:1]([NH:4][C:5](=[O:11])[CH2:6][CH2:7][CH2:8][CH2:9][Br:10])(=[O:3])[CH3:2].[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C(C)=CC=CC=1>[Br-:10].[C:1]([NH:4][C:5]([CH2:6][CH2:7][CH2:8][CH2:9][P+:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 64526622-Bromo-n-valeramide

Product 1

HCID 20488635HCID 20488635, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 50.5 g. (0.227 mole) of N-acetyl-5-bromovaleramide and 64.6 g. (0.274 mole) of triphenylphosphine in 250 ml. of xylene was heated at reflux under nitrogen for 4 hours then was let cool to room temperature. The xylene was decanted from the resulting oil which was recyrstallized from methylene chloride:ethyl acetate to afford colorless needles of [4-(acetylaminocarbonyl)butyl]triphenylphosphonium bromide weighing 50.2 g. (45.7% yield) melting at 164°-165°.

Workup

  1. temperatureat reflux under nitrogen for 4 hours
  2. customThe xylene was decanted from the resulting oil which

Sources & evidence

ORD record
ord-4bc31b9c815342399619e74599b2fc4f
Source dataset
uspto-grants-1976_05
Patent number
US03954741

Reaction notes

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