2-Iodobutane → 1-Tert-butyl-2-sec-butyl-4-(2-methylphenyl)-5-aminopyrazolin-3-one

HRID 362636Notes

Reaction equation

HRID 362636 reaction equation
[C:1]([N:5]1[CH:9]([NH2:10])[CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:7](=[O:18])[NH:6]1)([CH3:4])([CH3:3])[CH3:2].I[CH:20]([CH2:22][CH3:23])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:1]([N:5]1[CH:9]([NH2:10])[CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:7](=[O:18])[N:6]1[CH:20]([CH2:22][CH3:23])[CH3:21])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 105592-IodobutaneHCID 11430Potassium CarbonateHCID 698604911-Tert-butyl-4-(2-methylphenyl)-5-amino-pyrazolin-3-one

Product 1

HCID 698612641-Tert-butyl-2-sec-butyl-4-(2-methylphenyl)-5-aminopyrazolin-3-oneYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.23 g of 1-tert-butyl-4-(2-methylphenyl)-5-amino-pyrazolin-3-one, 1.84 g of 2-iodobutane, 2.1 g of potassium carbonate and 20 ml of ethanol was heated under reflux for 10 hours. The solvent was distilled off under reduced pressure, then, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate anhydride, then, the solvent was distilled off under reduced pressure. The residue was analyzed by 1H-NMR on the ratio of N-alkyl compound to O-alkyl compound being 16 to 84 was applied to column chromatography to obtain 250 ml (yield: 16%) of 1-tert-butyl-2-sec-butyl-4-(2-methylphenyl)-5-aminopyrazolin-3-one.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionwater was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate anhydride
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3d73969b5b604ed381ffb86255d374d8
Source dataset
uspto-grants-1999_02
Patent number
US05869684

Reaction notes

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