Chlorosulfonic acid → HCID 18541162, compound

HRID 411603Notes

Reaction equation

HRID 411603 reaction equation
[O:1]([CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O(CCN1CCOCC1)C1C=CC=CC=1.[Cl:32][S:33](O)(=[O:35])=[O:34]>ClCCl>[N:10]1([CH2:9][CH2:8][O:1][C:2]2[CH:7]=[CH:6][C:5]([S:33]([Cl:32])(=[O:35])=[O:34])=[CH:4][CH:3]=2)[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 24638Chlorosulfonic acid2×HCID 28409994-(2-phenoxyethyl)MorpholineHCID 6996069929488-54-8

Product 1

HCID 18541162HCID 18541162, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

[2-(Morpholin-4-yl)ethoxy]benzene-4-sulfonyl chloride was prepared using N-(2-phenoxyethyl) morpholine by similar reaction described above. For example, 7.2 g of N-(2-phenoxyethyl)morpholine HCl salt was resuspended in 20 ml of dichloromethane and 7 ml of chlorosulfonic acid was slowly introduced with cooling by ice-jacket. The reaction mixture was stirred at 0° C. for 2 hr, then, at room temperature overnight. Dichloromethane (350 ml) was added to the reaction mixture and excess chlorosulfonic acid was destroyed by adding icy water(about 100 g). Aqueous layer was adjusted to pH 8.5 by concentrated sodium carbonate solution with cooling by ice. Dichloromethane was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give 8.1 g of [2-(morpholin-4-yl)ethoxy]benzene-4-sulfonyl chloride. M.P. 48-50° C.

Workup

  1. custom[2-(Morpholin-4-yl)ethoxy]benzene-4-sulfonyl chloride was prepared
  2. customby similar reaction
  3. temperaturewith cooling by ice-jacket
  4. customat room temperature
  5. customovernight
  6. customwas destroyed
  7. additionby adding icy water(about 100 g)
  8. temperaturewith cooling by ice
  9. dry with materialDichloromethane was dried over anhydrous magnesium sulfate
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-dbb985ddc5d043828975100e1d40228c
Source dataset
uspto-grants-2003_05
Patent number
US06559167B1

Reaction notes

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