Water → HCID 56592442, compound

HRID 2359267Notes

Reaction equation

[H-].[Na+].[CH3:3][S:4]([NH2:7])(=[O:6])=[O:5].[Cl:8][C:9]1[C:10]([O:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([C:34]([F:37])([F:36])[F:35])[CH:28]=2)=[CH:11][C:12]([F:25])=[C:13]([CH:24]=1)[C:14](OC1C=CC(C)=CC=1)=[O:15].O>CC1CCCO1>[Cl:8][C:9]1[C:10]([O:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([C:34]([F:37])([F:35])[F:36])[CH:28]=2)=[CH:11][C:12]([F:25])=[C:13]([CH:24]=1)[C:14]([NH:7][S:4]([CH3:3])(=[O:6])=[O:5])=[O:15]

Participants

Conditions

Temperature: 65 °C

Procedure

To a suspension of sodium hydride (7.39 g, 184.66 mmol) in 2-methyltetrahydrofuran (400 mL) at 0-5° C. was added methanesulphonamide (16.47 g, 173.12 mmol) and the mixture stirred for 1 hour and allowed to reach room temperature. 4-Methylphenyl 5-chloro-4-[4-chloro-3-(trifluoromethyl)phenoxy]-2-fluorobenzoate (Preparation 163, 53 g, 115.41 mmol) in 2-methyltetrahydrofuran (100 mL) was added and the reaction mixture heated at 65° C. for 6 hours and cooled. Water (250 mL) was charged to the stirred reaction mixture and the layers separated. The organic layer was further washed with 1M citric acid solution (200 mL) and concentrated under reduced pressure at 45° C. The resulting solid was stirred in tert butyl methyl ether (250 mL) at 50° C. for 1 hour, cooled to 0-5° C., filtered and dried to give the title compound as an off-white solid (27.5 g, 53%).

Workup

customto reach room temperature
temperaturecooled
customthe layers separated
washThe organic layer was further washed with 1M citric acid solution (200 mL)
concentrationconcentrated under reduced pressure at 45° C
stirringThe resulting solid was stirred in tert butyl methyl ether (250 mL) at 50° C. for 1 hour
temperaturecooled to 0-5° C.
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-d8e1d6973a9246be83d4b8d0302579c9
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685977B2

Reaction notes

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