Hydrazine hydrate (1:1) → 4,4a,5,6-tetrahydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one

HRID 1728929Notes

Reaction equation

HRID 1728929 reaction equation
O=[C:2]1[CH:8]([CH2:9][C:10](O)=[O:11])[CH2:7][CH2:6][S:5][C:4]2[S:13][CH:14]=[CH:15][C:3]1=2.O.[NH2:17][NH2:18]>C(O)C>[N:17]1[NH:18][C:10](=[O:11])[CH2:9][CH:8]2[CH2:7][CH2:6][S:5][C:4]3[S:13][CH:14]=[CH:15][C:3]=3[C:2]=12

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 106339284-Oxo-4,5,6,7-tetrahydrothieno[2,3-b]thiepin-5-acetic acid

Product 1

HCID 190168224,4a,5,6-tetrahydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-oneYield 71.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2.0 g of 4-oxo-4,5,6,7-tetrahydrothieno[2,3-b]thiepin-5-acetic acid and 0.6 g of hydrazine hydrate in 20 ml of ethanol is refluxed under heating for 5 hours. After cooling, the precipitated crystals are collected by filtration and recrystallized from a mixed solvent of chloroform and ethanol to give 1.4 g of 4,4a,5,6-tetrahydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one as white crystals, melting at 215°-217° C.

Workup

  1. temperatureis refluxed
  2. temperatureunder heating for 5 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated crystals are collected by filtration
  5. customrecrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-8d3754efd7c24a238fa8f125484047d9
Source dataset
uspto-grants-1994_07
Patent number
US05329016

Reaction notes

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