(4-Chlorophenyl)hydrazine → HCID 19016812, compound

HRID 1728926Notes

Reaction equation

HRID 1728926 reaction equation
[CH3:1][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>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:12](=[O:14])[CH2:11][CH:8]3[CH2:7][S:6][C:5]4[S:15][C:2]([CH3:1])=[CH:3][C:4]=4[C:9]3=[N:24]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 15225036HCID 15225036, compound

Product 1

HCID 19016812HCID 19016812, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.0 g of 2-methyl-4-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-5-acetic acid and 2.0 g of 4-chlorophenylhydrazine in 50 ml of ethanol is refluxed under heating for 9 hours. After cooling, the 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 2.0 g of 2-(4-chlorophenyl)-8-methyl-4a,5-dihydro-2H-thieno[2',3':2,3]thiopyrano[4,5-c]pyridazin-3(4H)-one as pale brown crystals, melting at 142°-144° C.

Workup

  1. temperatureis refluxed
  2. temperatureunder heating for 9 hours
  3. temperatureAfter cooling
  4. concentrationthe mixture is concentrated under reduced pressure
  5. washeluted with chloroform
  6. customThe crystals obtained from the fraction
  7. customare recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-8709e7eb80314544b83b1dc76fd49879
Source dataset
uspto-grants-1994_07
Patent number
US05329016

Reaction notes

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