Triphenylphosphine → HCID 86651838, compound

HRID 1465446Notes

Reaction equation

HRID 1465446 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:11])=[CH:5][CH:4]=1.[C:21]1([P:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1C=CC=CC=1>[Cl-:1].[C:17]([O:16][C:14]([NH:13][NH:12][C:10]([CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][P+:27]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:4][CH:5]=1)=[O:11])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 67266620HCID 67266620, compound

Product 1

HCID 86651838HCID 86651838, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of tert-butyl 2-{[4-(chloromethyl)phenyl]acetyl}hydrazinecarboxylate (5.9 g, 19.7 mmol), triphenylphosphine (5.18 g, 19.7 mmol) and benzene (15 ml) was heated under reflux for 21 hrs. After cooling to room temperature, the precipitate was collected by filtration, washed 3 times with benzene, and dried under reduced pressure to give {4-[2-(tert-butoxycarbonyl)hydrazinocarbonylmethyl]benzyl}(triphenyl)phosphonium chloride (8.68 g, yield 78%) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 21 hrs
  3. filtrationthe precipitate was collected by filtration
  4. washwashed 3 times with benzene
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-d805eba4b89d4119a13c71d88d8163c5
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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