(Diethylamino)sulfur trifluoride → HCID 67499044, compound

HRID 661364Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1(O)[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1.C(N(S(F)(F)[F:23])CC)C>C(Cl)Cl>[F:23][C:6]1([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a −78° C. solution of the product of Example 27A (4.53 g, 17.77 mmol) in methylene chloride (50 mL) was added diethylaminosulfur trifluoride (DAST) (4.18 g, 3.97 mL, 30.0 mmol). The reaction mixture was stirred at −78° C. for four hours, then allowed to warm to ambient temperature, and stirred overnight. The reaction mixture was then cooled to 0° C., quenched with saturated aqueous sodium bicarbonate, and extracted with methylene chloride. The organic layer was separated and concentrated. The resulting residue was chromatographed on silica gel, eluting with 0%-15% ethyl acetate-hexane to obtain the title compound (3.55 g, 78%). 1H NMR (300 MHz, DMSO-d6) δ ppm 7.83 (m, 1H), 7.79 (m, 1H), 3.92 (s, 4H), 2.41-2.07 (m, 4H), 1.91-1.63 (m, 4H). MS (DCI) m/z 244 (M+H)+.

Workup

temperatureto warm to ambient temperature
stirringstirred overnight
temperatureThe reaction mixture was then cooled to 0° C.
customquenched with saturated aqueous sodium bicarbonate
extractionextracted with methylene chloride
customThe organic layer was separated
concentrationconcentrated
customThe resulting residue was chromatographed on silica gel
washeluting with 0%-15% ethyl acetate-hexane

Sources & evidence

ORD record: ord-00d840f1eece4819b7f1ed2f4c72196c
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084616B2

Reaction notes

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