تفاعل #1007349

معادلة التفاعل

NaHCO3

Lawesson's reagent

(R)-7-(5-bromo-2-fluoro-phenyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]nonan-9-one

Lawesson's reagent

→

(R)-7-(5-bromo-2-fluoro-phenyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]nonan-9-thione

المردود 91.8%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued at 80° C. for 8 hours
3. 3
   استخلاصextracted twice with ethyl acetate
4. 4
   غسيلThe organic layers were washed with brine
5. 5
   تجفيفdried over Na2SO4
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated
8. 8
   أخرىto give light yellow oil
9. 9
   أخرىThe residue was chromatographed on 20 g silica gel with 0-50% ethyl acetate in heptane

الإجراء التجريبي

To a solution of (R)-7-(5-bromo-2-fluoro-phenyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]nonan-9-one (1.1 g, 2.92 mmol, Eq: 1.00) in dioxane (50 ml) was added Lawesson's reagent (1.18 g, 2.92 mmol, Eq: 1.00). The reaction mixture was stirred at 80° C. for 2 hours. More Lawesson's reagent (1.55 g, 3.84 mmol, Eq: 1.00) was added and stirring continued at 80° C. for 8 hours. The reaction mixture was poured into sat. NaHCO3 solution and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to give light yellow oil. The residue was chromatographed on 20 g silica gel with 0-50% ethyl acetate in heptane to give (R)-7-(5-bromo-2-fluoro-phenyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]nonan-9-thione (1.05 g, 2.68 mmol, 91.5% yield) as a light yellow foam. MS (ISP): m/z=392.0 [M+H]+ and 394.3 [M+2+H]+.

المصدر