(4-Chlorophenyl)hydrazine → HCID 19016812, compound

HRID 1681827Notes

Reaction equation

HRID 1681827 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-3583ecf0596943cb88222f460c916bd3
Source dataset
uspto-grants-1992_12
Patent number
US05175162

Reaction notes

Loading…