Chlorosulfonic acid → HCID 86665720, compound

HRID 1619493Notes

Reaction equation

[F:1][C:2]([F:19])([F:18])[C:3]([N:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH2:6]1)=[O:4].[Cl:20][S:21](O)(=[O:23])=[O:22]>ClCCl>[CH3:17][O:16][C:11]1[CH:12]=[CH:13][C:14]([S:21]([Cl:20])(=[O:23])=[O:22])=[CH:15][C:10]=1[CH:7]1[CH2:8][CH2:9][N:5]([C:3](=[O:4])[C:2]([F:1])([F:18])[F:19])[CH2:6]1

Participants

Conditions

Temperature: -5 °C

Procedure

1.7 g of 2,2,2-trifluoro-1-(3-(2-methoxyphenyl)pyrrolidin-1-yl)ethanone (6.22 mmol) were dissolved in 5 mL of dichloromethane and the solution was cooled to −5° C. At this temperature, 14.5 g of chlorosulfonic acid (124 mmol) were slowly added dropwise. Stirring was continued for 1 h at −5° C. and 18 h at room temperature. The reaction was then cooled to 0° C. and slowly added into 30 g of a water/ice mixture. The suspension was extracted 5 times with 100 mL of dichloromethane and the combined organic phases were washed twice with 5% aqueous sodium hydrogencarbonate solution. The organic layer was dried over sodium sulfate, filtered, and the solvent was evaporated to yield 2.1 g of the title compound as a yellowish solid (storage in the refrigerator under argon atmosphere).

Workup

temperatureThe reaction was then cooled to 0° C.
extractionThe suspension was extracted 5 times with 100 mL of dichloromethane
washthe combined organic phases were washed twice with 5% aqueous sodium hydrogencarbonate solution
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
customthe solvent was evaporated

Sources & evidence

ORD record: ord-615faf40c57749a8879f567e4e8765bc
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772313B2

Reaction notes

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