Dichloromethane → HCID 17903124, compound

HRID 411602Notes

Reaction equation

HRID 411602 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:17][S:18](O)(=[O:20])=[O:19].ClCCl.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>C(Cl)(Cl)Cl>[N:11]1([CH2:10][CH2:9][CH2:8][O:1][C:2]2[CH:7]=[CH:6][C:5]([S:18]([Cl:17])(=[O:20])=[O:19])=[CH:4][CH:3]=2)[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24243Trisodium PhosphateHCID 24638Chlorosulfonic acid2×HCID 20574374-(3-phenoxypropyl)Morpholine2×

Product 1

HCID 17903124HCID 17903124, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

[3-(Morpholin-4-yl) propoxy] benzene-4-sulfonyl chloride was prepared by chlorosulfonylation of 4-(3-phenoxypropyl)morpholine using chlorosulfonic acid in the presence of dichloromethane or chloroform. For example, to a solution of 2.2 g (10 mmole) of N-(3-phenoxypropyl) morpholine in 20 ml of chloroform, 2 ml of chlorosulfonic acid (30 mmole) was slowly added at −10° C. and stirred for 30 min. The reaction mixture was stirred at room temperature for 5 hr. Chloroform was removed from lower layer. Lower layer was treated with chopped-ice to give solids. To a mixture of ice and solid product, 10 g of sodium phosphate (tribasic) was added and stirred with cooling. Chlorosulfonyl compound was extracted with dichloromethane (300 ml). Dichloromethane extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. 1.6 g of [3-(morpholin-4-yl) propoxy]benzene-4-sulfonyl chloride was obtained.

Workup

  1. customwas slowly added at −10° C.
  2. stirringThe reaction mixture was stirred at room temperature for 5 hr
  3. customChloroform was removed from lower layer
  4. additionLower layer was treated with chopped-ice
  5. customto give solids
  6. additionwas added
  7. stirringstirred
  8. temperaturewith cooling
  9. extractionChlorosulfonyl compound was extracted with dichloromethane (300 ml)
  10. extractionDichloromethane extract
  11. dry with materialwas dried over anhydrous magnesium sulfate
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-14553f9b63344fab999f7570f03c6b78
Source dataset
uspto-grants-2003_05
Patent number
US06559167B1

Reaction notes

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