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

HRID 1872948Notes

Reaction equation

HRID 1872948 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 (5C) 3N HCl and then with brine. The organic layer was dried (MgSO, 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 (5C) 3N HCl
  4. dry with materialThe organic layer was dried (MgSO
  5. concentrationconcentrated
  6. customto afford a thick, brown oil, 5.3 g

Sources & evidence

ORD record
ord-860704bf6ec04ecd95387999983c3d41
Source dataset
uspto-grants-2000_08
Patent number
US06110938

Reaction notes

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