تفاعل #1772012

ord-b0440208bb064fc9abb13d3d1bdff989

معادلة التفاعل

O=[N+]([O-])c1ccc(-c2nc3ccc(O)cc3s2)cc1
2-(4′-nitrophenyl)-6-hydroxy benzothiazole
CC(C)=O
acetone
O=C([O-])[O-].[K+].[K+]
K2CO3
CS(=O)(=O)Cl
MsCl
Cc1cc(OS(=O)(=O)O)c2nc(-c3ccc([N+](=O)[O-])cc3)sc2c1
2-(4-nitrophenyl)-6-methylsulfoxy benzothiazole
المردود 68.0%

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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 (30 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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08147798B2uspto-grants-2012_04