Triphenylphosphine → N-isobutyl acetamidotriphenylphosphonium chloride

HRID 2106866Notes

Reaction equation

HRID 2106866 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([NH:24][C:25](=[O:28])[CH2:26][Cl:27])[CH:21]([CH3:23])[CH3:22]>C1C=CC=CC=1>[Cl-:27].[CH2:20]([N:24]([P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:25](=[O:28])[CH3:26])[CH:21]([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 2223592-Chloro-N-isobutylacetamide

Product 1

HCID 23049290N-isobutyl acetamidotriphenylphosphonium chlorideYield 86%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of triphenylphosphine (229.8 g, 876 mmol) in dry benzene (800 ml) was added N-isobutyl-2-chloroacetamide (131 g, 876 mmol) (prepared by standard methods from 2-chloroacetyl chloride and isobutylamine) in dry benzene (100 ml). The solution was heated under reflux, with vigorous stirring, for 8 hours. Upon cooling, colourless needles formed. These were collected by filtration and the filtrate heated under reflux for a further 8 hours. A second batch of the produce was collected. The combined batches were washed with dry ether and dried in vacuo to give 310 g (86% of theory) of N-isobutyl-acetamidotriphenyl-phosphonium chloride as colourless needles.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux, with vigorous stirring, for 8 hours
  3. temperatureUpon cooling
  4. customcolourless needles formed
  5. filtrationThese were collected by filtration
  6. temperaturethe filtrate heated
  7. temperatureunder reflux for a further 8 hours
  8. customA second batch of the produce was collected
  9. washThe combined batches were washed with dry ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-4bc7284957884d8ba5eff9c5548684ed
Source dataset
uspto-grants-1990_06
Patent number
US04931469

Reaction notes

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