反応 #4908

反応方程式

2-[(1-methyl-3-pyrrolidinyl)thio]-3-pyridinecarboxylic acid

chloroform

triphenylphosphine

→

2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-thiazepin-5(4H)-one

溶媒

carbon tetrachloride

反応条件

後処理

1. 1
   温度at reflux for 2.5 hr
2. 2
   抽出The resulting solution was extracted with one 500 ml and three 125 ml portions of 1N hydrochloric acid
3. 3
   抽出extracted with isopropyl ether
4. 4
   抽出extracted three times with chloroform
5. 5
   抽出The combined chloroform extract
6. 6
   乾燥was dried over sodium sulfate
7. 7
   濃縮concentrated
8. 8
   その他A portion of the residue was chromatographed on the high pressure liquid chromatograph
9. 9
   その他The compound obtained
10. 10
    その他was crystallized from isopropyl ether-isopropyl alcohol, m.p. 97°-100° C.

実験手順

A mixture of 80.75 g (0.34 mole) of 2-[(1-methyl-3-pyrrolidinyl)thio]-3-pyridinecarboxylic acid, 500 ml of chloroform, 200 g of carbon tetrachloride and 178 g (0.68 mole) of triphenylphosphine was stirred at reflux for 2.5 hr. The resulting solution was extracted with one 500 ml and three 125 ml portions of 1N hydrochloric acid. The acid extracts were combined and extracted with isopropyl ether. The aqueous layer was basified with sodium hydroxide and extracted three times with chloroform. The combined chloroform extract was dried over sodium sulfate and concentrated. A portion of the residue was chromatographed on the high pressure liquid chromatograph using a silica column and ethyl acetate. The compound obtained was crystallized from isopropyl ether-isopropyl alcohol, m.p. 97°-100° C.

出典