(4-Chlorophenyl)hydrazine → HCID 19016808, compound

HRID 1728925Notes

Reaction equation

HRID 1728925 reaction equation
[Br:1][C:2]1[S:15][C:5]2[S:6][CH2:7][CH:8]([CH2:11][C:12]([OH:14])=O)[C:9](=O)[C:4]=2[CH:3]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][NH2:24])=[CH:19][CH:18]=1>C(O)C>[Br:1][C:2]1[S:15][C:5]2[S:6][CH2:7][CH:8]3[CH2:11][C:12](=[O:14])[N:23]([C:20]4[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=4)[N:24]=[C:9]3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 15225037HCID 15225037, compound

Product 1

HCID 19016808HCID 19016808, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.4 g of 2-bromo-4-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-5-acetic acid and 1.3 g of 4-chlorophenylhydrazine in 40 ml of ethanol is refluxed under heating for 14 hours. After cooling, the precipitated crystals are collected by filtration, washed with ethanol and then recrystallized from a mixed solvent of chloroform and ethanol to give 1.3 g of 8-bromo-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 169°-170° C.

Workup

  1. temperatureis refluxed
  2. temperatureunder heating for 14 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitated crystals are collected by filtration
  5. washwashed with ethanol
  6. customrecrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-abdc671d3c3843b0ac84e1f8f2c52b24
Source dataset
uspto-grants-1994_07
Patent number
US05329016

Reaction notes

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