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(Triphenylmethyl)thionyl Imide
(CAS RN:503596-47-2 Product Number:T3773)

Structure

(Triphenylmethyl)thionyl Imide
Synonym Tritylthionyl Imide
Synonym TrNSO

General Information

Product Number T3773

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Purity/Analysis Method >98.0%(GC)
Storage Temperature
M.F. / M.W. C19H15NOS=305.40
CAS RN 503596-47-2
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MDL Number
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Specification

Purity(GC) min. 98.0 %
Melting point 96.0 to 100.0 deg-C

Application

Sulfonimidamidation Reagent for Three-Component Reaction

T3773_02_1

Experimental procedure:(Triphenylmethyl)thionyl imide (50.0 mg, 0.164 mmol) is dissolved in THF (1 mL) at 0 °C. 4-Fluorophenylmagnesium bromide (178 μL, 0.164 mmol, 0.92 M in THF) is added dropwise and stirred for 5 min. tert-Butyl hypochlorite (19.5 μL, 0.172 mmol) is added in the dark and stirred for 15 min. After adding morpholine (30 μL, 0.344 mmol), the reaction mixture is stirred at room temperature for 22 h. Methanesulfonic acid (53 μL, 0.819 mmol, 5.0 equiv.) is added and the reaction stirs vigorously for 1 h at room temperature. After addition of CH2Cl2, the solution is washed with saturated aqueous sodium bicarbonate solution. The aqueous phase is extracted with CH2Cl2 three times. The combined organic layers are dried over sodium sulfate, filtered and concentrated. The residue is purified by flash chromatography (petrol/ethyl acetate, 3:1 to 1:2) to afford 4-(4-fluorophenylsulfonimidoyl)morpholine as a white solid (28 mg, 70% yield).

References

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