Water → HCID 20524749, compound

HRID 1702745Notes

Reaction equation

HRID 1702745 reaction equation
[OH:1][CH2:2][C:3](=[O:18])[CH2:4][N:5]([S:14]([CH3:17])(=[O:16])=[O:15])[C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13].[OH2:19].N1[CH:25]=[CH:24]C=CC=1>C(OC(=O)C)(=O)C.C(Cl)(Cl)Cl>[C:24]([O:1][CH2:2][C:3](=[O:18])[CH2:4][N:5]([S:14]([CH3:17])(=[O:16])=[O:15])[C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13])(=[O:19])[CH3:25]

Participants

6

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 20524772HCID 20524772, compound

Product 1

HCID 20524749HCID 20524749, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of N-(3-hydroxy-2-oxopropyl)-2',6'-dimethylmethanesulphonanilide (2.8 g) in pyridine (5 ml) and acetic anhydride (5 ml) was allowed to stand at room temperature for 20 hours. Water was added to decompose excess anhydride, and the oily product was extracted into ether. The ether solution was washed successively with dilute hydrochloric acid and sodium bicarbonate solution, dried (MgSO4), and evaporated to give a yellow oil. A solution of this oil in chloroform was percolated through a short column of silica gel. Evaporation of the eluate gave the product, N-(3-acetoxy-2-oxopropyl)-2',6'-dimethylmethanesulphonanilide, as a pale yellow oil.

Workup

  1. extractionthe oily product was extracted into ether
  2. washThe ether solution was washed successively with dilute hydrochloric acid and sodium bicarbonate solution
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a yellow oil
  6. customEvaporation of the eluate

Sources & evidence

ORD record
ord-21347049a07f434a9660eff9dc38db44
Source dataset
uspto-grants-1982_09
Patent number
US04349378

Reaction notes

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