Sodium Bicarbonate → HCID 67984877, compound

HRID 923758Notes

Reaction equation

[CH2:1]([S:3][C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]([NH:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[NH:19][CH3:20])=O)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C(C)=CC=CC=1>[CH2:1]([S:3][C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]1[N:19]([CH3:20])[C:10]2[CH:11]=[CH:12][C:13]([C:15]([F:18])([F:17])[F:16])=[CH:14][C:9]=2[N:8]=1)[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-ethylsulfanyl-N-(2-methylamino-5-trifluoromethylphenyl)-benzamide (1.64 g), p-toluenesulfonic acid monohydrate (1.76 g), and xylene (50 ml) was stirred under reflux at 150° C. for 1 hour. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.40 g of 2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as Present Compound 68).

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 and saturated brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9d4526677c1c46fbb9495a223e1a9b7b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278983B2

Reaction notes

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