Methyl iodide → [N-Methyl-N-(3-acetyl-phenyl)-amino]-triphenyl phosphonium iodide

HRID 464706Notes

Reaction equation

HRID 464706 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:10]=[P:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[CH3:30][I:31]>C1C=CC=CC=1>[I-:31].[CH3:30][N:10]([P+:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 541661621-{3-[(Triphenyl-lambda~5~-phosphanylidene)amino]phenyl}ethan-1-one

Product 1

HCID 20216403[N-Methyl-N-(3-acetyl-phenyl)-amino]-triphenyl phosphonium iodideYield 63%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 140.2 gm of 3-acetylphenyliminotriphenyl phosphorane and 56.9 gm of methyl iodide in 525 ml of dry benzene was refluxed for 8 hours in an atmosphere of nitrogen. The mixture was cooled, and the precipitate was filtered off, washed with benzene and dried, yielding 120 gm of the title compound, m.p. 178°-180° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitate was filtered off
  3. washwashed with benzene
  4. customdried

Sources & evidence

ORD record
ord-15b9d290955947c2b263ca0ea82ae566
Source dataset
uspto-grants-1985_10
Patent number
US04548944

Reaction notes

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