Chlorosulfonic acid → 4-methoxy-2-morpholin-4-yl-benzenesulfonic Acid

HRID 349696

Reaction equation

HRID 349696 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:4]=1.Cl[S:16]([OH:19])(=[O:18])=[O:17]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:16]([OH:19])(=[O:18])=[O:17])=[C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:4]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 99643354-(3-Methoxyphenyl)morpholine

Product 1

HCID 99001684-methoxy-2-morpholin-4-yl-benzenesulfonic AcidYield 20.3%

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred portion of 1-methoxy-3-morpholin-4-yl-benzene (1.08 g; 5.6 mmol) was added neat to chlorosulfonic acid (1.8 mL; 28 mmol) via pipette over 2 minutes under calcium sulfate-dried atmosphere. The resulting thick, red solution was allowed to warm to room temperature and stirred for 5 hours. The resulting solution was poured onto ice, then extracted with CH2Cl2 (3×50 mL). Combined organic layers then were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give the acid as a light green solid (0.31 g; 20%).

Workup

  1. customdried atmosphere
  2. temperatureto warm to room temperature
  3. additionThe resulting solution was poured onto ice
  4. extractionextracted with CH2Cl2 (3×50 mL)
  5. washCombined organic layers then were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c24c47c1c1045e0903bca7e91ee4268
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Linked notes

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