Triethylamine → HCID 19020329, compound

HRID 1109445Notes

Reaction equation

HRID 1109445 reaction equation
[NH2:1][O:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[Cl:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([Cl:26])[C:17]=1[N:27]1[C:31]([C:32](Cl)=[O:33])=[C:30]([C:35]#[N:36])[CH:29]=[N:28]1>C(OCC)C.O1CCCC1.C(OCC)(=O)C>[CH3:7][O:6][C:4]([CH2:3][O:2][NH:1][C:32]([C:31]1[N:27]([C:17]2[C:18]([Cl:26])=[CH:19][C:20]([C:22]([F:24])([F:25])[F:23])=[CH:21][C:16]=2[Cl:15])[N:28]=[CH:29][C:30]=1[C:35]#[N:36])=[O:33])=[O:5]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 22223HCID 22223, compoundHCID 54495530HCID 54495530, compound

Product 1

HCID 19020329HCID 19020329, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.31 g (0.022 mole) of methyl aminooxyacetate and 2.53 g (0.025 mole) of triethylamine in 70 mL of diethyl ether was cooled to -5° to 0° C. While this temperature was maintained, a solution of 7.4 g (0.020 mole) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-cyano-1H-5-pyrazolylcarboxylic acid chloride in 105 mL of tetrahydrofuran was added to the cooled solution during a 20 minute period. Upon completion of addition, the cooling bath was removed, and the resulting slurry was stirred at ambient temperature for 125 minutes. The slurry was filtered, and the filtrate was evaporated under reduced pressure, leaving a residue. This residue was dissolved in ethyl acetate, and this solution was washed twice with an aqueous solution of sodium chloride. The solution was then dried over anhydrous magnesium sulfate, filtered, and the solvent evaporated from the filtrate under reduced pressure, leaving a tacky solid residue weighing 8.54 g. This solid was triturated with petroleum ether for a period of approximately 17 hours. The resulting N-methoxycarbonylmethoxy-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-cyano-1H-5-pyrazolylcarboxamide, weighing 7.5 g, was recovered by filtration. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureWhile this temperature was maintained
  2. additionUpon completion of addition
  3. customthe cooling bath was removed
  4. filtrationThe slurry was filtered
  5. customthe filtrate was evaporated under reduced pressure
  6. customleaving a residue
  7. washthis solution was washed twice with an aqueous solution of sodium chloride
  8. dry with materialThe solution was then dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent evaporated from the filtrate under reduced pressure
  11. customleaving a tacky solid residue
  12. customThis solid was triturated with petroleum ether for a period of approximately 17 hours
  13. filtrationwas recovered by filtration

Sources & evidence

ORD record
ord-fbfa5825c12c49a68bd87b367800ff25
Source dataset
uspto-grants-1994_06
Patent number
US05321002

Reaction notes

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