4-Methoxybenzoic Acid → 4-Methoxy-3-(morpholine-4-sulfonyl)benzoic acid

HRID 277570Notes

Reaction equation

HRID 277570 reaction equation
[C:1]([OH:11])(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.Cl[S:13]([OH:16])(=O)=[O:14].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>O>[CH3:9][O:8][C:5]1[CH:4]=[CH:3][C:2]([C:1]([OH:11])=[O:10])=[CH:7][C:6]=1[S:13]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)(=[O:16])=[O:14]

Participants

5

Reactant 3

HCID 74784-Methoxybenzoic AcidHCID 8083MorpholineHCID 24638Chlorosulfonic acid

Product 1

HCID 7679134-Methoxy-3-(morpholine-4-sulfonyl)benzoic acidYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

p-Anisic acid (25.6 g, 168 mmol) was added neat to stirring chlorosulfonic acid (40 mL). This reaction was heated to 65° C. for 4 hours. The solution was poured very slowly into 500 mL of crushed ice, which was itself placed in a dry-ice/acetone bath to keep it cool. The water suspension that formed was allowed to stir for one hour, and it was then filtered. The solid was suspended in ether/dichloromethane (200 mL of 50/50), and excess morpholine (29 mL, 333 mmol) was added slowly. An immediate reaction occurred, but the reaction was allowed to stir overnight and then filtered and dried to provide the title compound (35 g, 69%). 1HNMR (DMSO-d6) δ13.2 (bs, 1H), 8.29 (d, J=2 Hz, 1H), 8.28 (dd, J=9 Hz, 2 Hz, 1H), 7.40 (d, J=9 Hz, 1H), 3.99 (s, 3H), 3.60 (m, 4H), 3.10 (m, 4H). MS (ES-POS): [M−H]=300.

Workup

  1. customplaced in a dry-ice/acetone bath
  2. temperaturecool
  3. filtrationit was then filtered
  4. customAn immediate reaction
  5. stirringto stir overnight
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-260d4998a00b437890ecab6a4d56dc00
Source dataset
uspto-grants-2002_03
Patent number
US06355633B1

Reaction notes

Loading…