Butanal → Diphenyl-1-(p-tolylsulfonylamino)butylphosphine oxide

HRID 438031Notes

Reaction equation

HRID 438031 reaction equation
[C:1]1([P:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:8]C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:21](=O)[CH2:22][CH2:23][CH3:24].[CH3:26][C:27]1[CH:28]=[CH:29][C:30]([S:33]([NH2:36])(=[O:35])=[O:34])=[CH:31][CH:32]=1>ClC1C=CC=CC=1>[C:15]1([P:7](=[O:8])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:21]([NH:36][S:33]([C:30]2[CH:31]=[CH:32][C:27]([CH3:26])=[CH:28][CH:29]=2)(=[O:34])=[O:35])[CH2:22][CH2:23][CH3:24])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 261ButanalHCID 6269P-ToluenesulfonamideHCID 11543680Phenoxydiphenylphosphine

Product 1

HCID 21427381Diphenyl-1-(p-tolylsulfonylamino)butylphosphine oxide

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
105 °C

Procedure

A white solid (60.6 g, 71% yield) separates when a mixture of 0.2 mole each of phenyl diphenylphosphinite, n-butyraldehyde, and p-toluenesulfonamide in 125 g of chlorobenzene is warmed at 105° C. for 1 hr. Recrystallization three times from o-dichlorobenzene gives a white solid product: mp 254°-263°; 31P nmr (CF3CO2H)- 44.7 ppm.

Workup

  1. customRecrystallization three times from o-dichlorobenzene
  2. customgives a white solid product

Sources & evidence

ORD record
ord-1469bfab5735472baa070acfa627cd1f
Source dataset
uspto-grants-1977_06
Patent number
US04032601

Reaction notes

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