Hydrochloric Acid → 5-Methanesulfonyl-pyridine-2-carboxylic acid (2-chloro-4-trifluoromethoxy-phenyl)-amide

HRID 509600Notizen

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[NH2:13].C[Al](C)C.[CH3:18][S:19]([C:22]1[CH:23]=[CH:24][C:25]([C:28](OC)=[O:29])=[N:26][CH:27]=1)(=[O:21])=[O:20].Cl>C1(C)C=CC=CC=1.ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:11])([F:12])[F:10])[CH:5]=[CH:4][C:3]=1[NH:13][C:28]([C:25]1[CH:24]=[CH:23][C:22]([S:19]([CH3:18])(=[O:21])=[O:20])=[CH:27][N:26]=1)=[O:29]

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

2-Chloro-4-trifluoromethoxy-phenylamine (2.0 g, 9.29 mmol) in toluene (50 mL) was added to trimethylaluminum (2.0 M 4.65 mL) then methyl 5-(methylsulfonyl)picolinate 6 (1.0 g, 4.65 mol) was added and the mixture was heated to 80-90° C. for 2 h. The reaction was cooled down and 1N HCl solution (10 mL) was added to be acidic. Dichloromethane (100 mL) was then added and the organic phase was further washed with water (100 mL) and dried over sodium sulfate. The solvent was removed and the residue was mixed with ether (50 mL) and stirred for 0.5 h. The solid was filtered and dried to give 5-methanesulfonyl-pyridine-2-carboxylic acid (2-chloro-4-trifluoromethoxy-phenyl)-amide 7 as a light yellow solid. Yield: 1.26 g, 65%.

Aufarbeitung

temperatureThe reaction was cooled down
washthe organic phase was further washed with water (100 mL)
dry with materialdried over sodium sulfate
customThe solvent was removed
additionthe residue was mixed with ether (50 mL)
filtrationThe solid was filtered
customdried

Quellen und Nachweise

ORD-Eintrag: ord-675cde833926421d9058a65d12f4f376
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09096587B2

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