Morpholine → Morpholine-4-sulfonyl chloride

HRID 1953447Notes

Reaction equation

HRID 1953447 reaction equation
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].C(N(CC)CC)C.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>ClCCl>[N:13]1([S:1]([Cl:5])(=[O:3])=[O:2])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 24648Sulfuryl chloride

Product 1

HCID 12798265Morpholine-4-sulfonyl chlorideYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under an ice-cooled, dichloromethane solution containing 12 ml (0.15 mol) of sulfurylchloride was cooled, dichloromethane solution containing 21 ml (0.15 mol) of triethylamine and 13 ml (0.15 mol) of morpholine was added dropwise over a period one hour. After stirring for 2 hour, the reaction mixture was washed cooled-0.1N hydrochloric acid and saturated brine and then was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue thus obtained was chromatographed on silica gel column for purification, whereby 20.54 g of morpholine-4-sulfonylchloride was obtained.

Workup

  1. temperatureUnder an ice-cooled
  2. temperaturewas cooled
  3. additionwas added dropwise over a period one hour
  4. washthe reaction mixture was washed
  5. temperaturecooled-0.1N hydrochloric acid and saturated brine
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. customwas chromatographed on silica gel column for purification

Sources & evidence

ORD record
ord-fcab8ffca9234b57a9669ab868c2759a
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

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