Propanal → HCID 21427384, compound

HRID 438029Notes

Reaction equation

HRID 438029 reaction equation
[P:1]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[O:2]C1C=CC=CC=1.[CH:23](=O)[CH2:24][CH3:25].[CH3:27][S:28]([NH2:31])(=[O:30])=[O:29]>ClC1C=CC=CC=1>[CH3:27][S:28]([NH:31][CH:23]([P:1](=[O:2])([O:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[O:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:24][CH3:25])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 527PropanalHCID 7540Triphenyl phosphiteHCID 72879Methanesulfonamide

Product 1

HCID 21427384HCID 21427384, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

When a mixture of 0.3 mole each of triphenyl phosphite, propionaldehyde, and methanesulfonamide in 150 g of chlorobenzene is stirred and warmed under nitrogen, heat of reaction is observed at about 100° C., and cooling is used for a few minutes to keep the temperature below 110° C., and cooling is used for a few minutes to keep the temperature below 110°. Warming is continued at 100°-110° for 2 hrs, and then the reaction mixture is stirred as it cools to room temperature, resulting in formation of a solid, 53.4 g (48% yield), of crude product. This is washed with water and recrystallized from benzene, giving white solid product: mp 136°-139°; 31P nmr (DMSO-d6)- 17.3 ppm.

Workup

  1. temperaturewarmed under nitrogen
  2. temperatureheat of reaction
  3. customis observed at about 100° C.
  4. temperaturecooling
  5. waitis used for a few minutes
  6. customthe temperature below 110° C.
  7. temperaturecooling
  8. waitis used for a few minutes
  9. customthe temperature below 110°
  10. temperatureWarming
  11. stirringthe reaction mixture is stirred as it
  12. customcools to room temperature
  13. customresulting in formation of a solid, 53.4 g (48% yield), of crude product
  14. washThis is washed with water
  15. customrecrystallized from benzene
  16. customgiving white solid product

Sources & evidence

ORD record
ord-225c5f012627493fa9fc3b189c212936
Source dataset
uspto-grants-1977_06
Patent number
US04032601

Reaction notes

Loading…