3-(Chlorosulfonyl)-4-fluorobenzoyl chloride → 5-[2-(1,3-dihydrobenzimidazol-2-ylidene)-3-(3-fluorophenyl)-3-oxopropanoyl]-2-fluorobenzenesulfonyl chloride

HRID 2423235Notes

Reaction equation

[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[F:14])[C:8](Cl)=[O:9])(=[O:4])=[O:3].[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[NH:17][C:16]1=[CH:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=1)=[O:26]>O1CCOCC1>[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[NH:17][C:16]1=[C:24]([C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=1)=[O:26])[C:8]([C:7]1[CH:11]=[CH:12][C:13]([F:14])=[C:5]([S:2]([Cl:1])(=[O:4])=[O:3])[CH:6]=1)=[O:9]

Participants

Conditions

Temperature: 110 °C

Procedure

At room temperature, 3-(chlorosulfonyl)-4-fluorobenzoyl chloride (3.19 g) was added to a dioxane (75 mL) suspension of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-(3-fluorophenyl)ethanone (1.50 g), followed by heating up to 110° C. and stirring for 1 hour. The reaction mixture was cooled to room temperature, the insoluble matter was separated by filtration, and then this was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to obtain 5-[2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-(3-fluorophenyl)-3-oxopropanoyl]-2-fluorobenzenesulfonyl chloride (2.10 g).

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe insoluble matter was separated by filtration
customthis was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-7d5aa8d61a984273a3cf36c6dc688a9b
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960562B2

Reaction notes

Loading…