تفاعل #2286388

معادلة التفاعل

NaHCO3

dichloromethane

N-methyl-N-(4-methyl-2-pyridin-3-yl-thiazol-5-yl)-3-methylsulfanyl-propionamide

Compound 19

N-methyl-N-(4-methyl-2-pyridin-3-yl-thiazol-5-yl)-3-methylsulfanyl-propionamide

sodium perborate tetrahydrate

→

desired product

المردود 65.0%

3-methanesulfonyl-N-methyl-N-(4-methyl-2-pyridin-3-yl-thiazol-5-yl)-propionamide

المردود 65.0%

المذيبات

acetic acid

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONThe reaction mixture was carefully poured into a separatory funnel
2. 2
   أخرىthe layers were separated
3. 3
   استخلاصThe aqueous layer was extracted twice with dichloromethane
4. 4
   تجفيفdried over MgSO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe crude product was purified by silica gel column chromatography (0 to 10% methanol/dichloromethane)

الإجراء التجريبي

To N-methyl-N-(4-methyl-2-pyridin-3-yl-thiazol-5-yl)-3-methylsulfanyl-propionamide (Compound 19, 132 mg, 0.43 mmol) in glacial acetic acid (4.0 mL) was added sodium perborate tetrahydrate (165 mg, 1.07 mmol), and the mixture was heated at 65° C. for 16 h. The reaction mixture was carefully poured into a separatory funnel containing saturated aqueous NaHCO3 resulting in gas evolution. When the gas evolution had ceased, dichloromethane was added and the layers were separated. The aqueous layer was extracted twice with dichloromethane, and all the organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (0 to 10% methanol/dichloromethane) to give the desired product as a white oil (77 mg, 65%): IR (KBr) 2927, 1675 cm−1; 1H NMR (300 MHz, CDCl3) δ 9.10 (d, J=2.0 Hz, 1H), 8.68 (dd, J=4.9, 1.7 Hz, 1H), 8.19 (dt, J=8.2, 2.0 Hz, 1H), 7.41 (dd, J=7.9, 4.9 Hz, 1H), 3.41 (t, J=6.9 Hz, 2H), 3.28 (s, 3H), 2.96 (s, 3H), 2.77 (t, J=7.3 Hz, 2H), 2.38 (s, 3H); ESIMS m/z 340.2 (M+1).

المصدر