Hydrazine, propyl- → HCID 53784436, compound

HRID 1576025Notes

Reaction equation

HRID 1576025 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[C:9]1[C:14](=O)[C:13](=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[CH2:12][S:11][CH2:10]1.[CH2:24]([NH:27][NH2:28])[CH2:25][CH3:26]>CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:27]([CH2:24][CH2:25][CH3:26])[N:28]=[C:14]2[C:13](=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:23])[CH2:12][S:11][CH2:10][CH:9]12

Participants

4

Reactant 2

HCID 42007Hydrazine, propyl-HCID 543246713,5-Bis[(2-methylphenyl)methylidene]thian-4-one

Product 1

HCID 53784436HCID 53784436, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6.7g of tetrahydro-3,5-bis-[(2-methylphenyl)methylene]-4H-thiopyran-4-one and 1.6g of n-propyl hydrazine in 250ml of methanol is heated at reflux temperature for 4 hours and allowed to cool to room temperature over a 16hour period. The precipitate that forms is collected by filtration and chromatographed on a neutral alumina column (Activity I). The fractions eluted with 10-20 % ether/hexane are combined and recrystallized from methanol/water to give 1.6g of the title compound, melting point 110°-112.5°C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 4 hours
  3. filtrationThe precipitate that forms is collected by filtration
  4. customchromatographed on a neutral alumina column (Activity I)
  5. washThe fractions eluted with 10-20 % ether/hexane
  6. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-7e535ef7512e4e089fbe4789692d53a8
Source dataset
uspto-grants-1976_09
Patent number
US03979381

Reaction notes

Loading…