تفاعل #217670

معادلة التفاعل

mono-brominated sulfonamide

1-(1-Benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-2-bromo-ethanone

potassium thioacetate

thioacetic acid

dichloromethane

→

Thioacetic acid S-[2-(1-benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-2-oxo-ethyl]ester

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added as a solid
2. 2
   workup.WAITis complete in minutes
3. 3
   أخرىEvaporation of the volatiles
4. 4
   أخرىleaves a tan residue which
5. 5
   ترشيحfiltered

الإجراء التجريبي

The mono-brominated sulfonamide from step 2 (0.194 g, 0.509 mmol) was was dissolved in methanol (2 ml) before potassium thioacetate (0.0639 g, 0.560 mmol) was added as a solid. LC-MS of the resulting yellow solution shows the reaction is complete in minutes. Evaporation of the volatiles leaves a tan residue which was taken up into dichloromethane (4 ml), during which the disulfide of the thioacetic acid was deposited and filtered. The desired thioester could then be recrystallized from dichloromethane/hexanes (0.080 g, 0.214 mmol, 42%). LC-MS (ES+): 376 [MH]+ m/e. 1H-NMR (DMSO): 7.87 (d, 3H), 7.78 (s, 1H), 7.7 (m, 1H), 7.57 (m, 3H), 4.41 (s, 2H), 3.99 (t, 2H), 3.06 (t, 2H), 2.34 (s, 3H)

المصدر