반응 #1368976

반응 방정식

Ethyl 2-(2-aminoanilino)benzo[b]thiophene-3-carboxylate

1-methylpiperazine

→

12-(4-methylpiperazin-1-yl)-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine

용매

anisole

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the completion of dropwise addition
2. 2
   workup.STIRRINGthe mixture was stirred at 140° C. for 20 hours
3. 3
   온도The reaction mixture was cooled to 80° C.
4. 4
   여과The resultant precipitate was filtrated
5. 5
   추출The filtrate was extracted with ethyl acetate (900 ml)
6. 6
   세척washed with saturated brine
7. 7
   건조dried over MgSO4
8. 8
   기타The solvent was evaporated under reduced pressure
9. 9
   기타The residue was purified by silica gel column chromatography (ethyl acetate/methanol)
10. 10
    workup.DISSOLUTIONthe obtained oily substance was dissolved in ethyl acetate (50 ml), to which
11. 11
    workup.ADDITIONwas added a solution (10 ml) of maleic acid (580 mg) in ethyl acetate
12. 12
    여과The precipitated crystals were collected by filtration
13. 13
    기타recrystallized from ethyl acetate/methanol

실험 절차

Ethyl 2-(2-aminoanilino)benzo[b]thiophene-3-carboxylate (3.5 g) and 1-methylpiperazine (20 ml) were dissolved in anisole (50 ml), titanium tetrachloride (3.1 ml) was added dropwise while stirring the mixture at room temperature. After the completion of dropwise addition, the mixture was stirred at 140° C. for 20 hours. The reaction mixture was cooled to 80° C. and poured into ice water. The resultant precipitate was filtrated. The filtrate was extracted with ethyl acetate (900 ml), washed with saturated brine, and dried over MgSO4. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) and the obtained oily substance was dissolved in ethyl acetate (50 ml), to which was added a solution (10 ml) of maleic acid (580 mg) in ethyl acetate. The precipitated crystals were collected by filtration and recrystallized from ethyl acetate/methanol to give 12-(4-methylpiperazin-1-yl)-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine.2 maleate (1.14 g).

출처