Hydrochloric Acid → 2-(4-Methoxy-phenyl)-1,1-dioxo-1lambda6-isothiazolidine-5-carbonitrile

HRID 1027589Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH2:13][C:14]#[N:15])(=[O:12])=[O:11])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24]Br.Cl>CN(C)C=O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:24][CH2:23][CH:13]([C:14]#[N:15])[S:10]2(=[O:12])=[O:11])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of the compound obtained in Step A (0.59 g) in dimethylformamide (40 ml) was added potassium carbonate (1.1 g). Then, a solution of 1,2-dibromoethane (0.59 g) in dimethylformamide (25 ml) was added dropwise at 55° C. The reaction mixture was then stirred at 55° C. for 2 hours, cooled to room temperature, poured into 15 ml water, and aqueous 2N hydrochloric acid was added to acidic pH. The aqueous layer was then extracted with dichloromethane, the combined organic layers washed two times with 2% aqueous hydrochloric acid, dried over sodium sulfate and concentrated in vacuo. Column chromatography (ethyl acetate/cyclohexane 7:3) afforded the title product as a beige solid (310 mg). 1HNMR (CDCl3, 400 MHz): 7.30 (d, 2H), 6.90 (d, 2H), 4.25 (m, 1H), (m, 1H), 3.70-3.90 (m, 5H), 2.95 (m, 1H), 2.80 (m, 1H).

Workup

temperaturecooled to room temperature
additionwas added to acidic pH
extractionThe aqueous layer was then extracted with dichloromethane
washthe combined organic layers washed two times with 2% aqueous hydrochloric acid
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-94e1aabcd59641f699cd72cc0351dbe5
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735362B2

Reaction notes

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