Hydrazine, propyl- → 2,3,3a,4,6,7-Hexahydro-3-phenyl-7-(phenylmethylene)-2-propylthiopyrano[4,3-c]pyrazole-5-oxide

HRID 1576020Notes

Reaction equation

HRID 1576020 reaction equation
[CH2:1]([NH:4][NH2:5])[CH2:2][CH3:3].[C:6]1([CH:12]=[C:13]2[C:18](=O)[C:17](=[CH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][S:15](=[O:27])[CH2:14]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CO>[C:6]1([CH:12]2[N:4]([CH2:1][CH2:2][CH3:3])[N:5]=[C:18]3[C:17](=[CH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:16][S:15](=[O:27])[CH2:14][CH:13]23)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 42007Hydrazine, propyl-HCID 681371553,5-Dibenzylidene-1lambda~4~-thiane-1,4-dione

Product 1

HCID 572446712,3,3a,4,6,7-Hexahydro-3-phenyl-7-(phenylmethylene)-2-propylthiopyrano[4,3-c]pyrazole-5-oxideYield 22.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

n-Propyl hydrazine (1.14g) is added to a suspension of 3.8g of tetrahydro-3,5-bis-(phenylmethylene)-4H-thiopyran-4-one-1-oxide in 75ml of methanol and the mixture is heated at reflux temperature for 2 hours. The crystals which form on cooling are collected to give 1.0g of the title compound, melting point 176°-177.5°C. The mother liquor is concentrated in vacuo and the residue is crystallized from acetonitrile/water (2:1) to yield an additional 0.6g of the title compound, melting point 176.5°-178°C. (isomer A)

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux temperature for 2 hours
  3. customThe crystals which form
  4. temperatureon cooling
  5. customare collected

Sources & evidence

ORD record
ord-a87b3f3398314ec4b13295593f321047
Source dataset
uspto-grants-1976_09
Patent number
US03979381

Reaction notes

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