Hydrochloric Acid → N-(2-hydroxy-5-trifluoromethylphenyl)-2-methylsulfanylbenzamide

HRID 923806Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[OH:12].[CH3:13][S:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](O)=[O:18].CCN=C=NCCCN(C)C.Cl>N1C=CC=CC=1>[OH:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=1[NH:1][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=1[S:14][CH3:13]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-amino-4-trifluoromethylphenol (1.00 g), 2-methylsulfanylbenzoic acid (0.95 g), WSC (1.41 g), and pyridine (20 ml) was stirred with heating at 80° C. for 2.5 hours. Into the reaction mixture cooled to room temperature, 1 mol/l of hydrochloric acid was poured, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine, sequentially, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.33 g of N-(2-hydroxy-5-trifluoromethylphenyl)-2-methylsulfanyl-benzamide (Compound (1B)-515).

Workup

temperatureInto the reaction mixture cooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine
dry with materialsequentially, dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-14fd5edd6a7d4f8192a0e905b50f96cd
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278983B2

Reaction notes

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