(4-Chlorophenyl)hydrazine → 2-(4-chlorophenyl)-4,4a, 5,6-tetrahydrothieno[2',3':2,3]thiopyrano[4,5-c]pyridazin-3(2H)-one

HRID 1728924노트

반응식

HRID 1728924 반응식
O=[C:2]1[CH:7]([CH2:8][C:9]([OH:11])=O)[CH2:6][S:5][C:4]2[S:12][CH:13]=[CH:14][C:3]1=2.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][NH2:23])=[CH:18][CH:17]=1>C(O)C>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:9](=[O:11])[CH2:8][CH:7]3[CH2:6][S:5][C:4]4[S:12][CH:13]=[CH:14][C:3]=4[C:2]3=[N:23]2)=[CH:18][CH:17]=1

참가 물질

4

반응물 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 152250354-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-5-acetic acid

생성물 1

HCID 190167892-(4-chlorophenyl)-4,4a, 5,6-tetrahydrothieno[2',3':2,3]thiopyrano[4,5-c]pyridazin-3(2H)-one수율 73.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 4.0 g of 4-oxo-5,6-dihydro-4H-thieno-[2,3-b]thiopyran-5-acetic acid and 3.3 g of 4-chlorophenylhydrazine in 70 ml of ethanol is refluxed under heating for 6.5 hours. After cooling, the reaction mixture is concentrated under reduced pressure. The residue is dissolved in 50 ml of acetic acid and the solution is refluxed under heating for 2 hours. Then, the resultant mixture is concentrated under reduced pressure, the residue is subjected to chromatography on silica gel and eluted with chloroform. The crystals obtained from the fraction are recrystallized from a mixed solvent of chloroform and ethanol to give 4.3 g of 2-(4-chlorophenyl)-4a,5-dihydro-2H-thieno[2',3':2,3]thiopyrano[4,5-c]pyridazin-3(4H)-one as pale brown crystals, melting at 162°-164° C.

후처리

  1. temperatureis refluxed
  2. temperatureunder heating for 6.5 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture is concentrated under reduced pressure
  5. dissolutionThe residue is dissolved in 50 ml of acetic acid
  6. temperaturethe solution is refluxed
  7. temperatureunder heating for 2 hours
  8. concentrationThen, the resultant mixture is concentrated under reduced pressure
  9. washeluted with chloroform
  10. customThe crystals obtained from the fraction
  11. customare recrystallized from a mixed solvent of chloroform and ethanol

출처 및 근거

ORD 기록
ord-b8bbf5850e4d4bb8aa19c64dad189136
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05329016

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