Water → N-(5-Methoxy-2-Phenoxyphenyl)methanesulfonamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:15][CH3:16])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(OCC)(=O)C.O>N1C=CC=CC=1>[CH3:17][S:18]([NH:1][C:2]1[CH:3]=[C:4]([O:15][CH3:16])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:20])=[O:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
10.0 g of 3-amino-4-phenoxyanisole was dissolved in 50 ml of pyridine. Thereto was dropwise added 5.59 g of methanesulfonyl chloride in 10 minutes with ice-cooling. The mixture was stirred for 1 hour at 20°-25° C. The reaction mixture was introduced into a mixture of 200 ml of ethyl acetate and 100 ml of water. The resulting organic layer was separated and washed with three 100-ml portions of 2N hydrochloric acid and then with a saturated aqueous sodium chloride solution. The organic layer was separated, dried with anhydrous magnesium sulfate, and subjected to distillation under reduced pressure to remove the solvent. The resulting crystal was recrystallized from isopropyl alcohol to obtain 12.5 g (yield: 91.9%) of 3-methylsulfonylamino4-phenoxyanisole having a melting point of 109.5°-111° C.
Workup
- customin 10 minutes
- temperaturecooling
- customThe resulting organic layer was separated
- washwashed with three 100-ml portions of 2N hydrochloric acid
- customThe organic layer was separated
- dry with materialdried with anhydrous magnesium sulfate
- distillationsubjected to distillation under reduced pressure
- customto remove the solvent
- customThe resulting crystal was recrystallized from isopropyl alcohol
Sources & evidence
- ORD record
- ord-dc64d8a783fa4f1bab6cca134ccd6bd3
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04954518
Reaction notes
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