1,5-Bis(p-chlorophenyl)-1,4-pentadien-3-one → HCID 178485181, compound

HRID 441679Notes

Reaction equation

HRID 441679 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.[IH:21].[NH2:22][NH:23][C:24]([NH:26][CH3:27])=[NH:25]>I.C(O)CC>[IH:21].[CH3:27][NH:26][C:24]([NH:23][N:22]=[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)=[NH:25]

Participants

5

Reactant 2

HCID 2299341,5-Bis(p-chlorophenyl)-1,4-pentadien-3-oneHCID 178485184HCID 178485184, compound

Product 1

HCID 178485181HCID 178485181, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 24841Hydrogen iodideCatalystHCID 10311-PropanolSolvent

Procedure

A mixture consisting of 3.03 grams of 1,5-bis(p-chlorophenyl)-1,4-pentadien-3-one, 2.16 grams of 1-amino-3-methylguanidine hydroiodide, 3 drops of 57 percent hydroiodic acid, and 50 ml. of n-propanol is stirred and heated under refluxing conditions for two hours. Cooling failed to yield a product. After concentration to about 15 ml. of volume, and addition of 60 ml. of ether, a yellow product is obtained. Recrystallization from ethanol gives 2.67 grams of the subject compound melting 213°-214.5° C.

Workup

  1. temperatureheated under refluxing conditions for two hours
  2. temperatureCooling
  3. customto yield a product
  4. concentrationAfter concentration to about 15 ml
  5. additionof volume, and addition of 60 ml
  6. customof ether, a yellow product is obtained
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-c8adbbd4eff848afb8b959c263d52a94
Source dataset
uspto-grants-1977_08
Patent number
USRE029358

Reaction notes

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