Pyridine → Methyl 2-[(methylsulfonyl)amino]benzoate
Reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].N1C=CC=CC=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(OCC)(=O)C>[CH3:18][S:19]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])(=[O:21])=[O:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Methyl anthranilate (11.73 g, 77.6 mmol) was dissolved in pyridine (25 mL, 309 mmol). Mixture was cooled to 0° C. Methanesulfonyl chloride (6.60 mL, 85.3 mmol) was added to the mixture drop-wise. Reaction mixture was warmed to room temperature and held with stirring overnight. Mixture was diluted with ethyl acetate. Material was washed twice with water and three times with 1N hydrochloric acid. Organic layer was dried (magnesium sulfate), filtered and then concentrated. Residue was triturated with 50% diethyl ether in hexanes. Solids were filtered off, washed with 50% diethyl ether-hexanes, washed with hexanes and then dried under high vacuum. Title compound was obtained as an off-white solid in 88% yield. MS m/e (M−H)−=227.9.
Workup
- customReaction mixture
- temperaturewas warmed to room temperature
- washMaterial was washed twice with water and three times with 1N hydrochloric acid
- dry with materialOrganic layer was dried (magnesium sulfate)
- filtrationfiltered
- concentrationconcentrated
- customResidue was triturated with 50% diethyl ether in hexanes
- filtrationSolids were filtered off
- washwashed with 50% diethyl ether-hexanes
- washwashed with hexanes
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-48ccc65ed5c84b2383ebf6e0ba173052
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470679B2
Reaction notes
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