Toluene → (N-n-Butylcarbamoyl)methyltriphenylphosphonium Chloride

HRID 1604468Notes

Reaction equation

HRID 1604468 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.C([CH:24]([Cl:28])[C:25]([NH2:27])=[O:26])CCC.[C:29]1([CH3:35])[CH:34]=[CH:33]C=CC=1>>[Cl-:28].[CH2:33]([NH:27][C:25]([CH2:24][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)=[O:26])[CH2:34][CH2:29][CH3:35]

Participants

4

Reactant 3

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 573063372-Chlorohexanamide

Product 1

HCID 19603925(N-n-Butylcarbamoyl)methyltriphenylphosphonium ChlorideYield 89.1%

Procedure

A solution of triphenyl phosphine (26.23 g, 0.1 mol) and n-butyl chloroacetamide (14.96 g, 0.1 mol) in toluene (250 mL) was refluxed with stirring for 22 h. After cooling to room temperature, the mixture was filtered and dried under high vacuum to afford 36.72 g (89.1% yield) of the title compound as white crystals. This material was used without further purification.

Workup

  1. filtrationthe mixture was filtered
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-83fb0f28c8c84517b1b7d7cc335a14b7
Source dataset
uspto-grants-1999_11
Patent number
US05994396

Reaction notes

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