Triethylamine → HCID 44819036, compound

HRID 1496901Notes

Reaction equation

HRID 1496901 reaction equation
Cl[C:2](=[N:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:21]12CC(C=C1)C=[CH:22]2.CCN(CC)CC>C1(C)C=CC=CC=1>[F:18][C:17]([F:20])([F:19])[O:16][C:13]1[CH:14]=[CH:15][C:10]([N:9]2[CH:22]=[CH:21][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:8]2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8473NorbornadieneHCID 75076919HCID 75076919, compound

Product 1

HCID 44819036HCID 44819036, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of hydrazonoyl chloride 65 (1.55 g, 4.99 mmol), bicyclo[2.2.1]hepta-2,5-diene (1.25 mL, 24.6 mmol) and Et3N (2.0 mL, 14.3 mmol) in toluene (10 mL) was heated to 70° C. for 1 h. The mixture was cooled and filtered, the filter cake was washed with toluene (10 mL) and the organic fractions were combined and evaporated. The residue was refluxed in xylenes (30 mL) for 2 h. Column chromatography on silica gel, eluting with hexanes, firstly gave xylenes, and then further elution with CH2Cl2 gave ethyl 1-[4-(trifluoromethoxy)phenyl]-1H-pyrazole-3-carboxylate (66) (1.176 g, 79%) as a white solid: mp 76-78° C.; 1H NMR (CDCl3) δ 7.91 (d, J=2.5 Hz, 1H), 7.79 (d, J=8.9 Hz, 2H), 7.33 (d, J=8.9 Hz, 2H), 7.00 (d, J=2.5 Hz, 1H), 4.44 (q, J=7.1 Hz, 2H), 1.43 (t, J=7.1 Hz, 3H). APCI MS m/z 301 [M+H]+.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washthe filter cake was washed with toluene (10 mL)
  4. customevaporated
  5. temperatureThe residue was refluxed in xylenes (30 mL) for 2 h
  6. washColumn chromatography on silica gel, eluting with hexanes, firstly gave xylenes
  7. washfurther elution with CH2Cl2

Sources & evidence

ORD record
ord-2f71276e82b942378ca0f235c27429c9
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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