Phenethyl bromide → 1-(2-Phenylethyl)-3-amino-4-ethoxycarbonylpyrazole

HRID 357897Notes

Reaction equation

HRID 357897 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][NH:6][N:5]=1.Br[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1>[C:17]1([CH2:16][CH2:15][N:6]2[CH:7]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([NH2:3])=[N:5]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 178469928HCID 178469928, compound

Product 1

HCID 221038291-(2-Phenylethyl)-3-amino-4-ethoxycarbonylpyrazoleYield 64.6%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

250 ml of toluene and 0.1 ml of aqueous 12.5M sodium hydroxide solution were added to a mixture of 15.69 g of ethyl 3-amino-4-pyrazolecarboxylate, 24.34 g of (2-bromoethyl)benzene, 2.54 g of Adogen 464 and 27.74 g of potassium carbonate, and heated under reflux for 2.5 hours. The reaction solution was washed with 200 ml of water and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (n-hexane-ethyl acetate=2:1→1:1→1:2) to obtain 16.94 g of 1-(2-phenylethyl)-3-amino-4-ethoxycarbonylpyrazole as colorless crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2.5 hours
  3. washThe reaction solution was washed with 200 ml of water
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-af901bc0790f4cba99e350b7d30c22f3
Source dataset
uspto-grants-1998_11
Patent number
US05840909

Reaction notes

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