Hydrochloric Acid → Benzenesulfonamide, 4-(hydroxymethyl)-N-methyl-
Reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][CH:7]=1)(=[O:5])=[O:4].Cl>O1CCCC1>[OH:11][CH2:10][C:9]1[CH:8]=[CH:7][C:6]([S:3]([NH:2][CH3:1])(=[O:5])=[O:4])=[CH:14][CH:13]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Add methyl amine (4.5 mL, 2 M in dichloromethane) to a mixture of 4-chlorosulfonyl benzoic acid (0.5 g) and dichloromethane (20 mL). Stir at room temperature overnight. Quench by pouring the reaction mixture into a mixture of saturated aqueous ammonium chloride and ethyl acetate. Separate the layers, wash the organic phase with water, dry the remaining organic phase over sodium sulfate and then concentrate under reduced pressure to provide (0.40 g, 82%) of an oil. Add borane-tetrahydrofuran complex (7.44 mL, 1 M) to a mixture of 4-methylsulfamoyl-benzoic acid (0.4 g) and tetrahydrofuran (10 mL) at 0° C. Heat at 80° C. for 3 hours. Cool at room temperature and add 1 N aqueous hydrochloric acid (20 mL) and extract with ethyl acetate. Wash with saturated aqueous sodium bicarbonate and dry the remaining organic phase over sodium sulfate and concentrate under reduced pressure to provide (0.28 g, 75%) of an oil.
Workup
- temperatureCool at room temperature
- extractionextract with ethyl acetate
- washWash with saturated aqueous sodium bicarbonate
- dry with materialdry the remaining organic phase over sodium sulfate
- concentrationconcentrate under reduced pressure
Sources & evidence
- ORD record
- ord-f707af3d727648f9a6a8a483e0334c30
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07320995B2
Reaction notes
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