HCID 178483585, compound → HCID 67598383, compound

HRID 1417171Notes

Reaction equation

HRID 1417171 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][N:10]=[C:11]([C:19](=[O:25])[CH:20]=[CH:21][N:22]([CH3:24])[CH3:23])[C:12](=[O:18])[CH:13]=[CH:14]N(C)C>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH:14]=[CH:13][C:12](=[O:18])[C:11]([C:19](=[O:25])[CH:20]=[CH:21][N:22]([CH3:24])[CH3:23])=[N:10]1

Participants

3

Reactant 1

HCID 178483585HCID 178483585, compound

Product 1

HCID 67598383HCID 67598383, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

1,7-bis(N,N-dimethylamino)-1,6-heptadien-3,4,5-trione 4-(2,4-dichlorophenyl)hydrazone (2.10 g) was dissolved in dry dichloromethane (6 ml), silica gel (19 g) was added and solvent was removed in vacuo. The mixture was heated at 80° C. for 30 minutes and then at 120° C. for 2 hours. After cooling, the product was extracted with acetone and the acetone was removed in vacuo. The oily residue was solidified with diethyl ether to afford 1-(2,4-dichlorophenyl)-3-[3-(N,N-dimethylamino)-1-oxo-2-propenyl]4(1H)-pyridazi- none (1.40 g), m.p. 152°-154° C.

Workup

  1. additionsilica gel (19 g) was added
  2. customsolvent was removed in vacuo
  3. temperatureAfter cooling
  4. extractionthe product was extracted with acetone
  5. customthe acetone was removed in vacuo

Sources & evidence

ORD record
ord-02a5a14ea3d14da0aa4cae0caeaba062
Source dataset
uspto-grants-1999_03
Patent number
US05877175

Reaction notes

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