Acetic Acid → HCID 54319289, compound

HRID 438027Notes

Reaction equation

HRID 438027 reaction equation
[P:1]([O-:7])([O-:6])[O:2][CH2:3][CH2:4][Cl:5].[CH:8](=O)[CH3:9].[CH:11]1[C:16]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:15][CH:14]=[C:13]([Cl:21])[CH:12]=1.C(O)(=O)C.[Cl:26][C:27]1C=CC=C[CH:28]=1>>[Cl:21][C:13]1[CH:12]=[CH:11][C:16]([S:17]([NH:20][CH:8]([P:1](=[O:7])([O:6][CH2:28][CH2:27][Cl:26])[O:2][CH2:3][CH2:4][Cl:5])[CH3:9])(=[O:19])=[O:18])=[CH:15][CH:14]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 7964ChlorobenzeneHCID 668244-ChlorobenzenesulfonamideHCID 21908521HCID 21908521, compound

Product 1

HCID 54319289HCID 54319289, compound

Procedure

When a mixture of 32.3 g of tris(2-chloroethyl phosphite, 5.8 g of freshly distilled acetaldehyde, 22.0 g of p-chlorobenzenesulfonamide, and 3.0 g of acetic acid in 100 g of chlorobenzene is stirred and warmed, heat of reaction is observed at about 90°. The temperature is kept at 95°-103° for 1 hr, and then the solvent and by-product are removed at reduced pressure. Ether is added to the residue, causing a solid to separate. This is washed with water and recrystallized from isopropyl alcohol, giving 12.4 g of white solid product: mp 94.5°-98°; 31P nmr (DMSO-d6)- 24.0 ppm.

Workup

  1. temperaturewarmed
  2. temperatureheat of reaction
  3. customis observed at about 90°
  4. customthe solvent and by-product are removed at reduced pressure
  5. additionEther is added to the residue
  6. customto separate
  7. washThis is washed with water
  8. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-4e9e53ef90df4a25b9331c90669026a5
Source dataset
uspto-grants-1977_06
Patent number
US04032601

Reaction notes

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