Hydrazine, propyl- → HCID 54067699, compound

HRID 1576016Notes

Reaction equation

HRID 1576016 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]2[C:15](=O)[C:14](=[CH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH2:13][S:12][CH2:11]2)=[CH:5][CH:4]=1.[CH2:26]([NH:29][NH2:30])[CH2:27][CH3:28]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:29]([CH2:26][CH2:27][CH3:28])[N:30]=[C:15]3[C:14](=[CH:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[CH2:13][S:12][CH2:11][CH:10]23)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 42007Hydrazine, propyl-HCID 286331HCID 286331, compound

Product 1

HCID 54067699HCID 54067699, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6.0g of tetrahydro-3,5-bis-[(4-methoxyphenyl)methylene]-4H-thiopyran-4-one and 1.3g of n-propyl hydrazine in 200 ml of methanol is heated at reflux temperature for 3.5 hours, and then allowed to cool to room temperature. The resultant crystals are collected by filtration and chromatographed on a dry packed neutral alumina column (Activity I). The fractions eluted with 10-20% ethyl acetate/hexane are combined and recrystallized from acetone/hexane to give 2.4g of the title compound, melting point 149.5°-151.5°C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 3.5 hours
  3. filtrationThe resultant crystals are collected by filtration
  4. customchromatographed on a dry
  5. washThe fractions eluted with 10-20% ethyl acetate/hexane
  6. customrecrystallized from acetone/hexane

Sources & evidence

ORD record
ord-094ba8f247a9475e9c0d0fd0d81c1fdc
Source dataset
uspto-grants-1976_09
Patent number
US03979381

Reaction notes

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