N-(2-Hydroxyethyl)aniline → HCID 13277505, compound

HRID 1462393Notes

Reaction equation

HRID 1462393 reaction equation
[Na].Cl[C:3]1[N:7]([CH3:8])[N:6]=[C:5]([CH3:9])[C:4]=1[C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18].[NH:20]([CH2:27][CH2:28][OH:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[NH:20]([CH2:27][CH2:28][O:29][C:3]1[N:7]([CH3:8])[N:6]=[C:5]([CH3:9])[C:4]=1[C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 31235N-(2-Hydroxyethyl)anilineHCID 5360545SodiumHCID 13020365(5-Chloro-1,3-dimethyl-1H-pyrazol-4-yl)(2,4-dichlorophenyl)methanone

Product 1

HCID 13277505HCID 13277505, compound

Procedure

0.08 g of sodium metal was dissolved with heating in 2 ml of 2-anilinoethanol, and then 1 g of 5-chloro-4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazole was added. The resulting mixture was heated at 100° to 110° C. for 3 hours with stirring. Excess 2-anilinoethanol was distilled off under reduced pressure. The residue was then washed with chloroform and filtered. The chloroform solution was washed with water and dried over anhydrous sodium sulphate. Chloroform was distilled off and the residue was purified by silica gel chromatography (eluent, benzene:acetone at 7:1) to give 0.92 g of the desired product, Compound 1, having a refractive index nD24 1.6105 (yield 69%).

Workup

  1. temperatureThe resulting mixture was heated at 100° to 110° C. for 3 hours
  2. distillationExcess 2-anilinoethanol was distilled off under reduced pressure
  3. washThe residue was then washed with chloroform
  4. filtrationfiltered
  5. washThe chloroform solution was washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. distillationChloroform was distilled off
  8. customthe residue was purified by silica gel chromatography (eluent, benzene:acetone at 7:1)

Sources & evidence

ORD record
ord-8771b403ee6a4c9a8a9c850bf19ac4c0
Source dataset
uspto-grants-1984_07
Patent number
US04460597

Reaction notes

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