반응 #322445

반응 방정식

N-methylformanilide

2-(4-methylphenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one

→

9-formyl-2-(4-methylphenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one

수율 59.4%

용매

oxychloride

반응 조건

후처리

1. 1
   workup.STIRRINGAfter stirring at room temperature for 2 hours
2. 2
   workup.ADDITIONthe mixture was poured into ice-cold water
3. 3
   추출extracted with chloroform
4. 4
   세척The extract was washed with water
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   농축concentrated in vacuo
7. 7
   기타The residue was chromatographed on a silica gel column
8. 8
   기타The solid was recrystallized from a mixed solvent of ethanol and ethyl acetate

실험 절차

A mixture of 4.7 g of N-methylformanilide in 3.3 ml of phosphrus oxychloride was stirred at room temperature for an hour and 5.4 g of 2-(4-methylphenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one was added thereto. After stirring at room temperature for 2 hours, the mixture was poured into ice-cold water and extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel column using a mixed solvent of hexane and ethyl acetate (2:1) as an eluent. The solid was recrystallized from a mixed solvent of ethanol and ethyl acetate to give 3.5 g of 9-formyl-2-(4-methylphenyl)-2,5,6,7-tetrahydro-3H-thieno-[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-one as a pale brown powder, melting at 127°-129° C.

출처