Benzenesulfonyl chloride → N-(4-Fluoro-3-trifluoromethyl-benzyl)-N-(1-methyl-1H-benzimidazol-2-yl)-benzenesulfonamide

HRID 885449Notes

Reaction equation

[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][NH:7][C:8]2[N:12]([CH3:13])[C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[N:9]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>N1C=CC=CC=1.CCOC(C)=O>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]([C:8]2[N:12]([CH3:13])[C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[N:9]=2)[S:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:32])=[O:31])=[CH:4][C:3]=1[C:20]([F:23])([F:21])[F:22]

Participants

Conditions

Temperature: 100 °C

Procedure

To (4-fluoro-3-trifluoromethyl-benzyl)-(1-methyl-1H-benzimidazol-2-yl)-amine (195 mg, 0.6 mmol) in anhydrous pyridine (3 mL) at room temperature was added benzenesulfonyl chloride (193 mg, 1.1 mmol). The resulting mixture was heated to 100° C. in a microwave reactor for 1 h; then diluted with EtOAc, washed with 1 N HCl, the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The resultant residue was purified by flash column chromatography (SiO2), eluting with a hexanes-EtOAc gradient to yield the title compound. MS 464 (M+1)+

Workup

washwashed with 1 N HCl
dry with materialthe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe resultant residue was purified by flash column chromatography (SiO2)
washeluting with a hexanes-EtOAc gradient

Sources & evidence

ORD record: ord-829554cab9fd4d159adb7aaab251f92a
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242157B2

Reaction notes

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