Dimethyl Sulfoxide → Methyl 2-fluoro-4-(4-thiomorpholinyl)benzoate

HRID 915919Notes

Reaction equation

CS(C)=O.[F:5][C:6]1[CH:15]=[C:14](F)[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9].[NH:17]1[CH2:22][CH2:21][S:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>O>[F:5][C:6]1[CH:15]=[C:14]([N:17]2[CH2:22][CH2:21][S:20][CH2:19][CH2:18]2)[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

To a 30 ml dimethyl sulfoxide solution of 3.44 g (20 mmol) of methyl 2,4-difluorobenzoate, 1.9 ml (20 mmol) of thiomorpholine and 2.76 g (20 mmol) of potassium carbonate were added, and the mixture was stirred at 80° C. Then, the reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. The washed system was dried over anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain 2.96 g (58%) of the captioned compound.

Workup

temperatureThen, the reaction mixture was cooled to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water
dry with materialThe washed system was dried over anhydrous sodium sulfate
distillationthe solvent was distilled off
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record: ord-09a2f5540fba48ada1133f40d491d951
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268128B2

Reaction notes

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