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

HRID 1728936Notes

Reaction equation

HRID 1728936 reaction equation
O=[C:2]1[CH:8]([CH2:9][C:10]([OH:12])=O)[CH2:7][CH2:6][S:5][C:4]2[S:13][CH:14]=[CH:15][C:3]1=2.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][NH2:24])=[CH:19][CH:18]=1>C(O)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:10](=[O:12])[CH2:9][CH:8]3[CH2:7][CH2:6][S:5][C:4]4[S:13][CH:14]=[CH:15][C:3]=4[C:2]3=[N:24]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 106339284-Oxo-4,5,6,7-tetrahydrothieno[2,3-b]thiepin-5-acetic acid

Product 1

HCID 106414982-(4-chlorophenyl)-4,4a,5,6-tetrahydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-oneYield 31.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.7 g of 4-oxo-4,5,6,7-tetrahydrothieno[2,3-b]thiepin-5-acetic acid and 2.6 g of 4-chlorophenylhydrazine in 50 ml of ethanol is refluxed under heating for 6.5 hours. Then, the reaction mixture is concentrated under reduced pressure. The resulting residue is dissolved in 40 ml of acetic acid and the solution is refluxed under heating for 1.5 hours. After cooling, the reaction mixture is concentrated under reduced pressure, the residue is subjected to column 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 1.7 g of 2-(4-chlorophenyl)-4,4a,5,6-tetrahydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one as pale brown crystals, melting at 134°-135° C.

Workup

  1. temperatureunder heating for 6.5 hours
  2. concentrationThen, the reaction mixture is concentrated under reduced pressure
  3. dissolutionThe resulting residue is dissolved in 40 ml of acetic acid
  4. temperaturethe solution is refluxed
  5. temperatureunder heating for 1.5 hours
  6. temperatureAfter cooling
  7. concentrationthe reaction mixture is concentrated under reduced pressure
  8. washeluted with chloroform
  9. customThe crystals obtained from the fraction
  10. customare recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-1baf05939936452995e1738580a4701d
Source dataset
uspto-grants-1994_07
Patent number
US05329016

Reaction notes

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