Hydrazine, propyl- → HCID 54120435, compound

HRID 1447800Notes

Reaction equation

HRID 1447800 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]2[C:15](=O)[C:14](=[CH:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=3)[CH2:13][S:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:26]([NH:29][NH2:30])[CH2:27][CH3:28]>CO.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([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]([Cl:24])=[C:20]([Cl:25])[CH:19]=4)[CH2:13][S:12][CH2:11][C:10]2=3)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 42007Hydrazine, propyl-HCID 5149244H-Thiopyran-4-one, 3,5-bis[(3,4-dichlorophenyl)methylene]tetrahydro-

Product 1

HCID 54120435HCID 54120435, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A suspension of tetrahydro-3,5-bis-(3,4-dichlorophenylmethylene)-4H-thiopyran-4-one (6.5 g, 15 mmole) and n-propylhydrazine (1.1 g, 15 mmole) in methanol/chloroform (1:1, 250 ml) is heated at reflux temperature overnight. When the reaction mixture is slightly cooled, unreacted starting material precipitates out and is removed (about 2.2 g) by filtration. The filtrate is concentrated in vacuo and dissolved in CHCl3 and washed with dilute HCl and water. The organic layer is dried (anhydrous MgSO4) and concentrated in vacuo to give 5 g of a semi-solid material. This is applied to a wet-packed (hexane) Al2O3 column (neutral, activity I), and eluted with 0-100% ether/hexane. The major product is obtained eluting with 10-40% ether/hexane. The later fractions, eluted with 50-80% ether/hexane, are combined, concentrated and the residue crystallized from MeOH/CHCl3 to give 0.4 g of the product in crystalline form (99% pure), m.p. 161°-162.5° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature overnight
  3. temperatureWhen the reaction mixture is slightly cooled
  4. customprecipitates out and
  5. customis removed (about 2.2 g)
  6. filtrationby filtration
  7. concentrationThe filtrate is concentrated in vacuo
  8. dissolutiondissolved in CHCl3
  9. washwashed with dilute HCl and water
  10. dry with materialThe organic layer is dried (anhydrous MgSO4)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03ce2a26e69741dc9b548ceb54c9463e
Source dataset
uspto-grants-1979_12
Patent number
US04178379

Reaction notes

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