Acetic Acid → HCID 23114807, compound

HRID 2080531Notes

Reaction equation

[C:1]([OH:4])(=[O:3])[CH3:2].[Cl:5][C:6]1[C:7]([CH:15]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])=[CH:8][C:9](CC#N)=[N:10][CH:11]=1.S(=O)(=O)(O)O>O>[Cl:5][C:6]1[C:7]([CH:15]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])=[CH:8][C:9]([CH2:2][C:1]([OH:4])=[O:3])=[N:10][CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To an acetic acid (2 ml) solution of [5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]acetonitrile (113 mg, 0.25 mmol) was added a mixture of water (2 ml) and concentrated sulfuric acid (2 ml) at room temperature. The resulting mixture was stirred at 100° C. for 2 hours. After the reaction mixture was cooled to room temperature, water was added thereto. The resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was washed with a mixed solvent of diethyl ether/hexane and then, collected by filtration to give the title compound (101 mg, 0.21 mmol, 86%) as a white solid.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
extractionThe resulting mixture was extracted with dichloromethane
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
customThe residue thus obtained
washwas washed with a mixed solvent of diethyl ether/hexane
filtrationcollected by filtration

Sources & evidence

ORD record: ord-11c7cd46533f42e292fbb59e8543d024
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932271B2

Reaction notes

Loading…