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

HRID 2211495Notes

Reaction equation

HRID 2211495 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, 0.036 mol) in pyridine (90 ml), cooled to 0° C., was added p-toluenesulfonyl chloride (13.6 g, 0.056 mol). 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 HCI 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 HCI
  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-ad9c261d229a4ca6b51eb6221626253d
Source dataset
uspto-grants-2006_09
Patent number
USRE039265E1

Reaction notes

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