Reaction #1884956

Reaction equation

2-(4′-nitrophenyl)-6-hydroxy benzothiazole

acetone

K2CO3

MsCl

→

2-(4-nitrophenyl)-6-methylsulfoxy benzothiazole

Yield 68.0%

Conditions

Workup

1. 1
   Filtrationthe reaction mixture was filtered
2. 2
   ConcentrationThe filtrate was concentrated
3. 3
   Otherthe residue was purified by flash column (silica gel, hexane:ethyl acetate=4:1)

Procedure

To a solution of 2-(4′-nitrophenyl)-6-hydroxy benzothiazole (50 mg, 0.18 mmol) dissolved in acetone (7 mL, anhydrous) was added K2CO3 (100 mg, 0.72 mmol, powdered) and MsCl (200 ul). After stirring for 2 hrs, the reaction mixture was filtered. The filtrate was concentrated and the residue was purified by flash column (silica gel, hexane:ethyl acetate=4:1) to give 2-(4-nitrophenyl)-6-methylsulfoxy benzothiazole (44 mg, 68%) as pale yellow solid. 1HNMR (300 MHz, acetone-d6) δ (ppm): 8.50-8.40(m, 4H), 8.29(d, J=2.3 Hz, 1H), 8.23(d, J=8.9 Hz, 1H), 7.61(dd, J1=2.3 Hz, J2=8.9 Hz, 1H).

Source