تفاعل #2286373

معادلة التفاعل

N-(1-methylcarbamoyl-ethyl)nicotinamide

Lawesson's reagent

→

desired product

المردود 68.7%

methyl-(4-methyl-2-pyridin-3-yl-thiazol-5-yl)-amine

المردود 68.7%

المذيبات

DCE

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate (NaHCO3)
2. 2
   أخرىThe layers were separated
3. 3
   غسيلthe organic layer was washed once with brine
4. 4
   تجفيفThe solution was dried over MgSO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىThe crude material was purified by silica gel column chromatography (ethyl acetate)

الإجراء التجريبي

To a 10 mL microwave vessel containing DCE (5 mL) was added N-(1-methylcarbamoyl-ethyl)nicotinamide (207 mg, 1.0 mmol) followed by Lawesson's reagent (2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide, 404 mg, 1.0 mmol) in one portion. The heterogeneous mixture was heated in a microwave for 5 min at 130° C. The reaction mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate (NaHCO3). The layers were separated and the organic layer was washed once with brine. The solution was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography (ethyl acetate) to give the desired product as an orange solid (141 mg, 68%): mp 84-87° C.; 1H NMR (300 MHz, CDCl3) δ 8.98 (d, J=1.7 Hz, 1H), 8.51 (dd, J=4.9, 1.7 Hz, 1H), 8.08 (dt, J=8.0, 1.7 Hz, 1H), 7.29 (m, 1H), 3.00 (s, 3H), 2.30 (s, 3H); ESIMS m/z 206.4 (M+1), m/z 204.2 (M−1).

المصدر