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

HRID 1681838Notes

Reaction equation

HRID 1681838 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 fo 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
  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-45f156fc894e41debd85f71b0157d21a
Source dataset
uspto-grants-1992_12
Patent number
US05175162

Reaction notes

Loading…