N-Methylaniline → 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-[2-(N-methylanilino)ethoxy]pyrazole

HRID 1462394Notes

Reaction equation

HRID 1462394 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[N:9]([CH3:10])[N:8]=[C:7]([CH3:11])[C:6]=1[C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20].[CH3:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[C:12]([C:6]1[C:7]([CH3:11])=[N:8][N:9]([CH3:10])[C:5]=1[O:4][CH2:3][CH2:2][N:23]([CH3:22])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]

Participants

3

Reactant 2

HCID 7515N-MethylanilineHCID 13361374HCID 13361374, compound

Product 1

HCID 132775064-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-[2-(N-methylanilino)ethoxy]pyrazole

Procedure

A mixture of 1.1 g of 5-(2-bromoethoxy)-4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazole and 6 ml of N-methylaniline was heated at 110° to 120° C. for 3 hours with stirring. Excess N-methylaniline was distilled off under reduced pressure. The residue was then purified by silica gel chromatography (eluent, benzene:ethyl acetate at 10:1) to give 0.71 g of the desired product, Compound 2, having a refractive index nD24 1.5975 (yield 60.5%).

Workup

  1. temperaturewas heated at 110° to 120° C. for 3 hours
  2. distillationExcess N-methylaniline was distilled off under reduced pressure
  3. customThe residue was then purified by silica gel chromatography (eluent, benzene:ethyl acetate at 10:1)

Sources & evidence

ORD record
ord-bb23f638975d486e829f3453d6dc75ad
Source dataset
uspto-grants-1984_07
Patent number
US04460597

Reaction notes

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