Water → 4-[(4-Bromobenzene)sulfonyl]morpholine

HRID 2249279Notes

Reaction equation

HRID 2249279 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.O>N1C=CC=CC=1>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8083Morpholine

Product 1

HCID 2531284-[(4-Bromobenzene)sulfonyl]morpholineYield 88.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.67 g (19.14 mmol) of morpholine in 50 ml of dry pyridine was added 3.26 g (12.76 mmol) of 4-bromobenzenesulfonyl chloride in an atmosphere of argon, and the mixture was allowed to react at 0° C for 3 hours. To the solution was added water followed by extraction with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane yielded 3.45 g (11.3 mmol) of N-(4-bromobenzenesulfonyl)morpholine.

Workup

  1. customto react at 0° C for 3 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas subjected to silica gel column chromatography for separation and purification
  7. washElution with dichloromethane

Sources & evidence

ORD record
ord-165b58fc597046b1b658bb01ae64d305
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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