Benzyl Chloride → HCID 15703582, compound

HRID 1457921Notes

Reaction equation

HRID 1457921 reaction equation
[Na].[O-]CC.[Na+].[NH2:6][C:7]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][NH:9][N:8]=1.[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[NH2:6][C:7]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][N:9]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 178469928HCID 178469928, compound

Product 1

HCID 15703582HCID 15703582, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (1.9 g) was dissolved in anhydrous ethanol (100 ml) to prepare a solution of sodium ethoxide. To this, were added 3-amino-4-ethoxycarbonylpyrazole (12.4 g) and benzyl chloride (10 g), and the resulted mixture was refluxed for 1 h. After filtration of the hot mixture, the filtrate was concentrated to quarter volume, and cooled to crystallize. The crude product was recrystallized from an ether-water mixture to give 3-amino-1-benzyl-4-ethoxycarbonylpyrazole (10.7 g, yield 44%). To a solution of 3-amino-1-benzyl-4-ethoxycarbonylpyrazole (0.2 g) in dried toluene (30 ml), were added propyl isocyanate (0.307 ml) and triethylamine (0.11 ml), and the mixture was refluxed in a sealed tube for 8 h. The reaction mixture was evaporated under reduced pressure followed by silica-gel column chromatography (toluene : ethyl acetate=20:1) to give the title compound (0.129 g, yield 48%). 1H-NMR (CDCl3) δ ppm: 0.92 (3H, t, J=7Hz, CH2CH2CH3 ), 1.32 (3H, t, J=7Hz, COOCH2CH3 ), 1.57 (2H, 6th, CH2CH2CH3), 4.28 (2H, q, J=7Hz, COOCH2CH3), 5.14 (2H, s, CH2 --Ph), 7.25 (5H, m, CH2 --Ph), 7.91 (2H, brs, NH), 8.00 (1H, s, C5-H)

Workup

  1. temperaturethe resulted mixture was refluxed for 1 h
  2. filtrationAfter filtration of the hot mixture
  3. concentrationthe filtrate was concentrated to quarter volume
  4. temperaturecooled
  5. customto crystallize
  6. customThe crude product was recrystallized from an ether-water mixture

Sources & evidence

ORD record
ord-a02e43171bad4746a8cfcd92ddefad56
Source dataset
uspto-grants-1998_12
Patent number
US05849779

Reaction notes

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