p-Bromobenzenesulfonyl chloride → 4-[(4-Bromobenzene)sulfonyl]morpholine

HRID 1961505Notes

Reaction equation

HRID 1961505 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>ClCCl>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8083MorpholineHCID 8471Triethylamine

Product 1

HCID 2531284-[(4-Bromobenzene)sulfonyl]morpholine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Morpholine (58.2 mg, 0.668 mmol) and triethylamine (116 μl, 0.835 mmol) were placed in a round-bottom flask with a stir bar. Dry dichloromethane (5870 μL) was then added and the solution cooled to 0° C. 4-bromobenzenesulfonyl chloride (150 mg, 0.556 mmol) was added and the reaction was allowed to warm to room temperature overnight. It was quenched with water and extracted in ethyl acetate. The organic layers were washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 4-[(4-bromophenyl)sulfonyl]morpholine as a white solid.

Workup

  1. temperatureto warm to room temperature overnight
  2. customIt was quenched with water
  3. extractionextracted in ethyl acetate
  4. washThe organic layers were washed with aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a2f68b771e3e45bcae7988929118a79d
Source dataset
uspto-grants-2013_04
Patent number
US08415346B2

Reaction notes

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