Triphenylphosphine → HCID 19608850, compound

HRID 1075847Notes

Reaction equation

HRID 1075847 reaction equation
[C:1]([NH:9][C:10](=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14][Br:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[Br-:15].[C:1]([NH:9][C:10]([CH2:11][CH2:12][CH2:13][CH2:14][P+:23]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 21541105HCID 21541105, compound

Product 1

HCID 19608850HCID 19608850, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.84 g. (10 mmoles) of the N-benzoyl-5-bromovaleramide prepared above and 3.93 g. (15 mmoles) of triphenylphosphine in 50 ml. of acetonitrile was heated at reflux, under nitrogen, for 72 hours. The acetonitrile was removed by rotary evaporation and the resultant solid was triturated with benzene (3×) then was recrystallized from methylene chloride:ethyl acetate to afford the desired [4-benzoylaminocarbonylbutyl]-triphenylphosphonium bromide weighing 2.38 g. (43.7% yield) melting at 193°-194°.

Workup

  1. temperatureat reflux, under nitrogen, for 72 hours
  2. customThe acetonitrile was removed by rotary evaporation
  3. customthe resultant solid was triturated with benzene (3×)
  4. customthen was recrystallized from methylene chloride

Sources & evidence

ORD record
ord-7afffa1e6457494382e61d501b291860
Source dataset
uspto-grants-1976_05
Patent number
US03954741

Reaction notes

Loading…