Triethylamine → HCID 71087792, compound

HRID 1520780Notes

Reaction equation

HRID 1520780 reaction equation
Cl[C:2](=[N:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([F:19])[F:18])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:20]12CC(C=C1)C=[CH:21]2.C(N(CC)CC)C>C1(C)C=CC=CC=1.C1(C)C(C)=CC=CC=1>[F:18][CH:17]([F:19])[O:16][C:13]1[CH:14]=[CH:15][C:10]([N:9]2[CH:21]=[CH:20][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:8]2)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8473NorbornadieneHCID 86674809HCID 86674809, compound

Product 1

HCID 71087792HCID 71087792, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 2-chloro-2-(2-(4-(difluoromethoxy)phenyl)hydrazono)acetate (585 mg, 2 mmol) was dissolved in toluene (4 ml) and 2,5-norbornadiene (906 mg, 1 ml, 9.83 mmol) and triethylamine (587 mg, 808 μl, 5.8 mmol) were added. The reaction mixture was stirred at 70° C. for 30 min and the reaction mixture was allowed to stir at room temperature overnight. The solid was filtered off and washed with toluene. The organic fraction was evaporated and the residue obtained was dissolved in xylene (12 ml) and refluxed for 2 hours. The solvent was evaporated and the residue was purified by column chromatography (50 g Silicagel, dichloromethane) to yield 387 mg (69%) of a light yellow solid. MS (ISP): 283.1 ([M+H]+).

Workup

  1. stirringto stir at room temperature overnight
  2. filtrationThe solid was filtered off
  3. washwashed with toluene
  4. customThe organic fraction was evaporated
  5. customthe residue obtained
  6. temperaturerefluxed for 2 hours
  7. customThe solvent was evaporated
  8. customthe residue was purified by column chromatography (50 g Silicagel, dichloromethane)

Sources & evidence

ORD record
ord-631b9b48fc9745d4b994bbf97cdae81c
Source dataset
uspto-grants-2015_07
Patent number
US09073911B2

Reaction notes

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