1-Propanol → 3-(4-Iodophenyl)-1-(4-cyanophenyl)-4-ethoxycarbonyl-2-methyl-2H-pyrazol-5-one

HRID 1740084Notes

Reaction equation

HRID 1740084 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10][CH3:11])=[CH:5][CH:4]=1)#[N:2].[I:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](Cl)=[C:20]([C:26]([O:28]CC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C.C(O)CC>C(OCC)(=O)C>[I:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:10]([CH3:11])[N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)[C:26](=[O:28])[C:20]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 10311-PropanolHCID 81531DiisopropylethylamineHCID 21837631Ethyl 3-(4-iodophenyl)-3-chloro-2-ethoxycarbonylacrylateHCID 218376391-(4-Cyanophenyl)-2-methylhydrazine

Product 1

HCID 218376333-(4-Iodophenyl)-1-(4-cyanophenyl)-4-ethoxycarbonyl-2-methyl-2H-pyrazol-5-oneYield 55.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 29.34 g of 1-(4-cyanophenyl)-2-methylhydrazine, 65.17 g of ethyl 3-(4-iodophenyl)-3-chloro-2-ethoxycarbonylacrylate, 30.9 g of diisopropylethylamine and 300 ml of 1-propanol was refluxed under heating for 17 hours, then cooled and stirred with 200 ml of ethyl acetate at room temperature for 20 hours. The precipitated crystals were collected by filtration and washed with hexane-ethyl acetate to give 42.21 g of the title compound as pale yellow crystals.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 17 hours
  3. temperaturecooled
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with hexane-ethyl acetate

Sources & evidence

ORD record
ord-3734deefe61c458d894b3070703105b0
Source dataset
uspto-grants-1999_10
Patent number
US05968967

Reaction notes

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