Triethylamine → HCID 22101087, compound

HRID 1457922Notes

Reaction equation

HRID 1457922 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.[CH2:19]([N:22]=[C:23]=[O:24])[CH2:20][CH3:21].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:19]([NH:22][C:23]([NH:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1)=[O:24])[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61033Propyl isocyanateHCID 15703582HCID 15703582, compound

Product 1

HCID 22101087HCID 22101087, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 mixture was refluxed in a sealed tube for 8 h
  2. customThe reaction mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-006c4e7c57434fd3b6f88c3301e632b0
Source dataset
uspto-grants-1998_12
Patent number
US05849779

Reaction notes

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