Benzenesulfonyl chloride → N-Propyl-N-(2-hydroxyethyl)benzenesulfonamide
Reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][OH:7])[CH2:2][CH3:3].[C:8]1([S:14](Cl)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:4]([CH2:5][CH2:6][OH:7])[S:14]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:16])=[O:15])[CH2:2][CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
At 0° C., 5.16 g (50 mmol) of N-propylethanolamine were introduced into 70 ml of methylene chloride, and 9.7 g (55 mmol) of benzenesulfonyl chloride and 7.6 g (75 mmol) of triethylamine were added successively. After 2 hours of stirring at 0° C., the mixture was allowed to warm to room temperature, stirring was continued for a further hour and the mixture was then extracted with 1M hydrochloric acid and subsequently with 2M aqueous sodium hydroxide solution. The organic phase was dried over Na2SO4, filtered, concentrated and the resulting residue (13.2 g) was chromatographed over silica gel (methylene chloride/methanol 19:1). Yield: 7.4 g as an oil which was directly reacted further.
Workup
- additionwere added successively
- temperatureto warm to room temperature
- stirringstirring
- waitwas continued for a further hour
- extractionthe mixture was then extracted with 1M hydrochloric acid and subsequently with 2M aqueous sodium hydroxide solution
- dry with materialThe organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customthe resulting residue (13.2 g) was chromatographed over silica gel (methylene chloride/methanol 19:1)
- customYield: 7.4 g as an oil which was directly reacted further
Sources & evidence
- ORD record
- ord-b3465bdbcac6485f9fbde1792e9f90fa
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06509341B1
Reaction notes
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