Hydrazine, propyl- → HCID 54501544, compound

HRID 1447802Notes

Reaction equation

HRID 1447802 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[NH:30][N:29]([CH2:26][CH2:27][CH3:28])[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][C:10]2=3)=[CH:5][CH:4]=1

Participants

4

Reactant 2

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

Product 1

HCID 54501544HCID 54501544, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tetrahydro-3,5-bis-(4-methoxyphenyl-methylene)-4H-thiopyran-4-one (6 g, 17 mmole) and propylhydrazine (1.4 g, 19 mmole) in methanol (250 ml) is heated at reflux temperature for 4.5 hours. After the reaction mixture is left at room temperature overnight, yellow solids precipitate out and are collectd by filtration. The crude product is applied to a Al2O3 column (Activity I, neutral). The major product is eluted with 10-20% ethyl acetate/acetic acid. Continued elution with 10-60% CHCl3 /hexane yields the title compound. Recrystallization from acetone/hexane gives 0.65 g of final product in crystalline form (99% pure), m.p. 131.5°-133.5°.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 4.5 hours
  3. customyellow solids precipitate out and
  4. filtrationare collectd by filtration
  5. washThe major product is eluted with 10-20% ethyl acetate/acetic acid
  6. washContinued elution with 10-60% CHCl3 /hexane

Sources & evidence

ORD record
ord-b333823f90cc425395bfc10ce3d7da9b
Source dataset
uspto-grants-1979_12
Patent number
US04178379

Reaction notes

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