Hydrazine, propyl- → HCID 53955405, compound

HRID 1576022Notes

Reaction equation

HRID 1576022 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[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]([Cl:24])=[C:20]([Cl:25])[CH:19]=4)[CH2:13][S:12][CH2:11][CH:10]23)[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 53955405HCID 53955405, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A suspension of 6.5g of tetrahydro-3,5-bis-[(3,4-dichlorophenyl)methylene]-4H-thiopyran-4-one and 1.1g of n-propyl hydrazine in 250ml of methanol/chloroform (1:1) is heated at reflux temperature for about 16 hours. The reaction mixture is allowed to cool slightly. Unreacted starting material precipitates out and is removed by filtration. The filtrate is concentrated in vacuo, added to chloroform and washed with dilute hydrochloric acid and water. The organic layer is dried with magnesium sulfate and concentrated in vacuo to 5g of a semi-solid material. This is applied to a wet-packed (hexane) neutral alumina column (Activity I) and eluted with 0-100% ether/hexane. Elution with 10-40% ether/hexane yields the product as an oil.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for about 16 hours
  3. temperatureto cool slightly
  4. customprecipitates out and
  5. customis removed by filtration
  6. concentrationThe filtrate is concentrated in vacuo
  7. additionadded to chloroform
  8. washwashed with dilute hydrochloric acid and water
  9. dry with materialThe organic layer is dried with magnesium sulfate
  10. concentrationconcentrated in vacuo to 5g of a semi-solid material
  11. washeluted with 0-100% ether/hexane
  12. washElution with 10-40% ether/hexane

Sources & evidence

ORD record
ord-53165c105d484d6daa35662fa3809940
Source dataset
uspto-grants-1976_09
Patent number
US03979381

Reaction notes

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