Triethylamine → HCID 11984250, compound
Reaction equation
C(N(CC)CC)C.Cl.[CH3:9][C:10](=[CH2:17])[C:11]([O:13][CH2:14][CH2:15][NH2:16])=[O:12].[F:18][C:19]([F:25])([F:24])[S:20](F)(=[O:22])=[O:21]>C1C2NC3C(=CC=CC=3)SC=2C=CC=1.C(#N)C>[CH3:17][C:10](=[CH2:9])[C:11]([O:13][CH2:14][CH2:15][NH:16][S:20]([C:19]([F:25])([F:24])[F:18])(=[O:22])=[O:21])=[O:12]Participants
Conditions
- Temperature
- -30 °C
Procedure
In a 1 L three-neck flask equipped with a thermometer and a reflux condenser were placed 350 g of acetonitrile, 70.7 g (0.699 mol) of triethylamine, 33.1 g (0.200 mol) of 2-aminoethyl 2-methylacrylate hydrochloride, and 0.2 g of phenothiazine, followed by cooling to −30° C. with stirring. After the inner temperature reached −30° C., 36.5 g (0.240 mol) of trifluoromethanesulfonyl fluoride was introduced into the slurry as a gas over a period of 1 hour. After completion of the introduction, the mixture was continued to stir for further 1 hour and then warmed to room temperature. The solvent acetonitrile and unreacted trifluoromethanesulfonyl fluoride were removed by evaporation from the reaction solution under reduced pressure. One litter of diisopropyl ether was added thereto to form a suspension and the precipitated triethylamine hydrochloride and triethylamine hydrofluoride were removed by filtration. To the filtrate was added 200 mL of an 18% aqueous calcium chloride solution, followed by washing and separation into two layers. Furthermore, the organic layer was washed with 200 g of a 10% aqueous sodium chloride solution three times. The organic layer was dried over 40 g of magnesium sulfate. After removal of the magnesium sulfate by filtration, 0.2 g of phenothiazine was added thereto and the solvent was removed by evaporation to obtain 44.2 g of a crude organic matter. The crude organic matter was distilled under reduced pressure and a fraction of 105 to 115° C./13 Pa was collected, whereby 36.0 g of 2-{[(trifluoromethyl)sulfonyl]amino}ethyl 2-methylacrylate was obtained. Gas chromatographic investigation of composition thereof revealed that objective 2-{[(trifluoromethyl)sulfonyl]amino}ethyl 2-methylacrylate was 97.5%. The resulting organic matter was crystallized from diisopropyl ether/n-hexane to obtain 32.4 g of white crystals. Gas chromatographic investigation of composition thereof revealed that objective 2-{[(trifluoromethyl)sulfonyl]amino}ethyl 2-methylacrylate was 99.0%. The yield was 61.4%.
Workup
- customIn a 1 L three-neck flask equipped with a thermometer and a reflux condenser
- customreached −30° C.
- stirringto stir for further 1 hour
- temperaturewarmed to room temperature
- customThe solvent acetonitrile and unreacted trifluoromethanesulfonyl fluoride were removed by evaporation from the reaction solution under reduced pressure
- additionOne litter of diisopropyl ether was added
- customto form a suspension
- customthe precipitated triethylamine hydrochloride and triethylamine hydrofluoride were removed by filtration
- additionTo the filtrate was added 200 mL of an 18% aqueous calcium chloride solution
- washby washing
- customseparation into two layers
- washFurthermore, the organic layer was washed with 200 g of a 10% aqueous sodium chloride solution three times
- dry with materialThe organic layer was dried over 40 g of magnesium sulfate
- customAfter removal of the magnesium sulfate
- filtrationby filtration, 0.2 g of phenothiazine
- additionwas added
- customthe solvent was removed by evaporation
- customto obtain 44.2 g of a crude organic matter
- distillationThe crude organic matter was distilled under reduced pressure
- customa fraction of 105 to 115° C./13 Pa was collected
Sources & evidence
- ORD record
- ord-f08478993b39493584828abf9a9ade61
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115771B2
Reaction notes
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