3'-Aminoacetophenone → 1-{3-[(Triphenyl-lambda~5~-phosphanylidene)amino]phenyl}ethan-1-one

HRID 464705Notes

Reaction equation

HRID 464705 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1)=[O:3].C(N(CC)CC)C.[Br-].[Br-].[C:20]1([P:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)(Cl)(Cl)Cl>[C:2]([C:4]1[CH:5]=[C:6]([N:10]=[P:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 74173'-AminoacetophenoneHCID 8471TriethylamineHCID 12890784Triphenylphosphane dibromide

Product 1

HCID 541661621-{3-[(Triphenyl-lambda~5~-phosphanylidene)amino]phenyl}ethan-1-oneYield 70.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A mixture of 67.6 gm of 3-amino acetophenone, 101.2 gm of triethylamine and 100 ml of carbon tetrachloride was added to a stirred suspension of 211 gm of triphenylphosphine dibromide in 1700 ml of carbon tetrachloride. After 20 minutes of refluxing, the mixture was filtered and evaporated to dryness. The residual solid was treated with isopropanol, filtered and dried, yielding 140.2 gm of the title compound, m.p. 135°-136° C.

Workup

  1. temperatureAfter 20 minutes of refluxing
  2. filtrationthe mixture was filtered
  3. customevaporated to dryness
  4. additionThe residual solid was treated with isopropanol
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-b4eb071dbd0f427998958f9404a1524d
Source dataset
uspto-grants-1985_10
Patent number
US04548944

Reaction notes

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