Acetaldehyde → Phenyl [1-(p-tolylsulfonylamino)ethyl]phenylphosphinate

HRID 438030

Reaction equation

HRID 438030 reaction equation
[C:1]1([P:7]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:8]C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:22](=O)[CH3:23].[CH3:25][C:26]1[CH:27]=[CH:28][C:29]([S:32]([NH2:35])(=[O:34])=[O:33])=[CH:30][CH:31]=1>ClC1C=CC=CC=1>[C:26]1([CH3:25])[CH:27]=[CH:28][C:29]([S:32]([NH:35][CH:22]([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:8])[O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:23])(=[O:34])=[O:33])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 6269P-ToluenesulfonamideHCID 239038Diphenyl phenylphosphonite

Product 1

HCID 54172963Phenyl [1-(p-tolylsulfonylamino)ethyl]phenylphosphinateYield 79%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 0.15 mole each of diphenyl phenylphosphonite, acetaldehyde, and p-toluenesulfonamide in 100 g of chlorobenzene is stirred and warmed at 103°-115° C. for 1 hr, and the solvent and by-product phenol are removed by concentration of the reaction mixture to 120° at 0.5 mm. Ether is stirred into the residue, causing separation of 49.4g (79% yield) of solid product. Recrystallization twice from chlorobenzene gives a white solid: mp 178°-181°; 31P nmr (DMSO-d6)- 37.7 ppm.

Workup

  1. temperaturewarmed at 103°-115° C. for 1 hr
  2. customthe solvent and by-product phenol are removed by concentration of the reaction mixture to 120° at 0.5 mm
  3. stirringEther is stirred into the residue

Sources & evidence

ORD record
ord-01c96d3c130a4e90a40e60e0bc6f3664
Source dataset
uspto-grants-1977_06
Patent number
US04032601

Linked notes

Loading…