Pyridine → HCID 22719106, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].N1C=CC=CC=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([OH:10])=[C:2]([NH:1][S:18]([CH3:17])(=[O:20])=[O:19])[CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
10 g of 2-amino-4-methoxyphenol was dissolved in 100 ml of methylene chloride. 17 ml of pyridine was added thereto and the mixture was cooled to 5° C. Then, 9.1 g of methanesulfonyl chloride was added dropwise in 10 minutes and stirring gas conducted for 1 hour at 5°-10° C. The solvent was removed by distillation under reduced pressure. To the residue were added 100 ml of ethyl acetate and 50 ml of water. The mixture was adjusted to pH 2 with 4N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from isopropyl alcohol to obtain 14.4 g (yield: 92%) of 4-methoxy-2-methylsulfonylaminophenol having a melting point of 135°-136° C.
Workup
- customThe solvent was removed by distillation under reduced pressure
- additionTo the residue were added 100 ml of ethyl acetate and 50 ml of water
- customThe organic layer was separated
- washwashed with water
- dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
- customThe solvent was removed by distillation under reduced pressure
- customThe residue was recrystallized from isopropyl alcohol
Sources & evidence
- ORD record
- ord-b2b1f74acbbf47b79330ba19eda9bfd5
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04954518
Reaction notes
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