4-Toluenesulfonyl chloride → N-[2-(3-phenylsulfonyloxypropoxy)phenyl]acetamide

HRID 370156Notes

Reaction equation

HRID 370156 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13](=[O:15])[CH3:14].[C:16]1(C)[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>N1C=CC=CC=1>[C:19]1([S:22]([O:1][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:12][C:13](=[O:15])[CH3:14])(=[O:24])=[O:23])[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chloride2×HCID 21960061HCID 21960061, compound

Product 1

HCID 21960096N-[2-(3-phenylsulfonyloxypropoxy)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-[2-(3-hydroxypropoxy)phenyl]-acetamide (Example 113) (7.5 g, 36 mmol) in pyridine (90 ml), cooled to 0° C., was added p-toluenesulfonyl chloride (13.6 g, 56 mmol). After the tosyl chloride went into solution, the reaction was then allowed to stand at 5° C. for 16 hours. The reaction was poured onto ice, and a brown oil settled. The aqueous supernatant was decanted from the oil, and the residual oil taken up in diethyl ether. The diethyl ether was washed with cold (5° C.) 3N HCl and then with brine. The organic layer was dried (MgSO4), and concentrated to afford a thick, brown oil, 5.3 g.

Workup

  1. additionThe reaction was poured onto ice
  2. customThe aqueous supernatant was decanted from the oil
  3. washThe diethyl ether was washed with cold (5° C.) 3N HCl
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customto afford a thick, brown oil, 5.3 g

Sources & evidence

ORD record
ord-e33f28ebc50c46149c7a97dddc0e6a91
Source dataset
uspto-grants-2000_10
Patent number
US06140345

Reaction notes

Loading…