Chlorosulfonic acid → HCID 59563966, compound
Reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH2:7][CH2:6]1)=[O:4].[Cl:20][S:21](O)(=[O:23])=[O:22]>ClCCl>[CH3:17][C:12]1[CH:13]=[CH:14][C:15]([S:21]([Cl:20])(=[O:23])=[O:22])=[CH:16][C:11]=1[N:8]1[CH2:7][CH2:6][N:5]([C:3](=[O:4])[C:2]([F:1])([F:18])[F:19])[CH2:10][CH2:9]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
To a solution of 2 g of 2,2,2-trifluoro-1-(4-o-tolyl-piperazin-1-yl)-ethanone (7.35 mmol) in 5 mL of dichloromethane at −5° C. were slowly added 19.7 g of chlorosulfonic acid (169 mmol). After stirring for 2 h at −5° C., the reaction mixture continued stirring for 16 h, thereby slowly allowed to warm to room temperature. After cooling to 0° C., the reaction mixture was slowly added to a water/ice mixture. The aqueous phase was extracted five times with dichloromethane, the combined organic phases washed with aqueous sodium bicarbonate solution and saturated sodium chloride solution. The organic layer was dried over magnesium sulphate, filtered, and the solvent evaporated to yield 2.2 g of product as a white solid.
Workup
- customat −5° C.
- stirringthe reaction mixture continued stirring for 16 h
- temperatureto warm to room temperature
- temperatureAfter cooling to 0° C.
- extractionThe aqueous phase was extracted five times with dichloromethane
- washthe combined organic phases washed with aqueous sodium bicarbonate solution and saturated sodium chloride solution
- dry with materialThe organic layer was dried over magnesium sulphate
- filtrationfiltered
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-fee7100cf31a45cfa10fd9fe9978b7f6
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710059B2
Reaction notes
Loading…