Butanal → HCID 53759850, compound

HRID 438028Notes

Reaction equation

HRID 438028 reaction equation
[P:1]([O-:7])([O-:6])[O:2][CH2:3][CH2:4][Cl:5].[CH:8](=O)[CH2:9][CH2:10][CH3:11].[CH3:13][S:14]([NH2:17])(=[O:16])=[O:15].[Cl:18][C:19]1C=CC=C[CH:20]=1>>[CH3:13][S:14]([NH:17][CH:8]([P:1](=[O:7])([O:6][CH2:20][CH2:19][Cl:18])[O:2][CH2:3][CH2:4][Cl:5])[CH2:9][CH2:10][CH3:11])(=[O:16])=[O:15]

Participants

5

Reactant 4

HCID 261ButanalHCID 7964ChlorobenzeneHCID 72879MethanesulfonamideHCID 21908521HCID 21908521, compound

Product 1

HCID 53759850HCID 53759850, compound

Procedure

A mixture of 74.1 g (0.275 mole) of tris(2-chloroethyl phosphite, 19.8 g (0.275 mole) of n-butyraldehyde, and 23.8 g (0.25 mole) of methanesulfonamide in 130 ml of chlorobenzene is stirred and warmed at 90°-110° under nitrogen for 5.5 hrs, and then the solvent and ethylenechlorohydrin by-product are removed at reduced pressure. Ether (100 ml) is added to the residue, resulting in formation of a white solid after several hours. Recrystallization from carbon tetrachloride gives 33.2 g: mp 69°-72°; 31P nmr (CDCl3)- 24.4 ppm.

Workup

  1. temperaturewarmed at 90°-110° under nitrogen for 5.5 hrs
  2. customthe solvent and ethylenechlorohydrin by-product are removed at reduced pressure
  3. additionEther (100 ml) is added to the residue
  4. customresulting in formation of a white solid after several hours
  5. customRecrystallization from carbon tetrachloride
  6. customgives 33.2 g

Sources & evidence

ORD record
ord-79dd52d59ec240169e084d35f11f6f39
Source dataset
uspto-grants-1977_06
Patent number
US04032601

Reaction notes

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