1,5-Bis(p-chlorophenyl)-1,4-pentadien-3-one → HCID 73791714, compound

HRID 441680Notes

Reaction equation

HRID 441680 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=O)[CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Br.[NH:22]1[CH2:26][CH2:25][N:24]=[C:23]1[NH:27][NH2:28]>Br.C(O)CC>[ClH:1].[NH:24]1[CH2:25][CH2:26][N:22]=[C:23]1[NH:27][N:28]=[C:10]([CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH:9]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 2299341,5-Bis(p-chlorophenyl)-1,4-pentadien-3-oneHCID 30850992-Hydrazino-delta-2-imidazoline hydrobromide

Product 1

HCID 73791714HCID 73791714, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 10311-PropanolSolvent

Conditions

Temperature
-10 °C

Procedure

A mixture consisting of 6 grams of 1,5-bis(p-chlorophenyl)- 1,4-pentadien-3-one, 3.6 grams of 2-imidazolin-2-ylhydrazine hydrobromide, 10 drops of 48 percent aqueous hydrobromic acid and 80 ml. of n-propanol is stirred and heated at reflux for two hours. The reaction mixture is then concentrated to about one-half its volume and cooled at -10° C. The yellow crystalline precipitate is collected, washed with ether, and then added to a slight excess of aqueous 2N sodium hydroxide. The resultant free base is collected, dried, dissolved in ether and treated with a slight excess of 7.2 N n-propanolic hydrogen⟦,⟧ chloride, yielding the title compound melting at 239°-240° C. If the original hydrobromide salt is recrystallized from methanol, a product containing one mole of methanol of crystallization is obtained, melting at 206.5°-208.5° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for two hours
  3. concentrationThe reaction mixture is then concentrated to about one-half its volume
  4. customThe yellow crystalline precipitate is collected
  5. washwashed with ether
  6. additionadded to a slight excess of aqueous 2N sodium hydroxide
  7. customThe resultant free base is collected
  8. customdried
  9. dissolutiondissolved in ether
  10. additiontreated with a slight excess of 7.2 N n-propanolic hydrogen⟦,⟧ chloride

Sources & evidence

ORD record
ord-786c1cfa5f404bddaef8b4ab5a3fbac0
Source dataset
uspto-grants-1977_08
Patent number
USRE029358

Reaction notes

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