Pyridine → 2-Methyl-4-methoxy-5-mesylaminophenyl mesylate
Reaction equation
N1C=CC=CC=1.[CH3:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([NH2:16])=[CH:10][C:9]=1[OH:17].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>O>[S:19]([O:17][C:9]1[CH:10]=[C:11]([NH:16][S:19]([CH3:18])(=[O:21])=[O:20])[C:12]([O:14][CH3:15])=[CH:13][C:8]=1[CH3:7])(=[O:21])(=[O:20])[CH3:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
20 ml of pyridine was cooled to 0° C. and 2.10 g (3.70 mmol) of 2-methyl-4-methoxy-5-aminophenol and 5.3 g (46.2 mmol) of methanesulfonyl chloride were added thereto. The mixture was adjusted to room temperature followed by stirring for 1 hour. Then 200 ml of water was poured thereto and the mixture was extracted with 300 ml of chloroform, and the extra was washed with 2N hydrochloric acid and a saturated aqueous solution of sodium hydrogencarbonate and dried over anhydrous Glauber's salt. After distilling off the solvent under reduced pressure, brown crystals were obtained. These crystals were purified by column chromatography (the same as the one used in Example 3) and recrystallized from the solvent mixture of ethyl acetate/hexane (2:1). Thus 2.01 g (6.50 mmol) of 2-methyl-4-methoxy-5-mesylaminophenyl mesylate was obtained. The yield was 47%.
Workup
- customwas adjusted to room temperature
- extractionthe mixture was extracted with 300 ml of chloroform
- washthe extra was washed with 2N hydrochloric acid
- dry with materiala saturated aqueous solution of sodium hydrogencarbonate and dried over anhydrous Glauber's salt
- distillationAfter distilling off the solvent under reduced pressure
- custombrown crystals were obtained
- customThese crystals were purified by column chromatography (the same as the one
- customrecrystallized from the solvent mixture of ethyl acetate/hexane (2:1)
Sources & evidence
- ORD record
- ord-51f567f228074e9ba815fa67bfc68d85
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05104414
Reaction notes
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