Ethyl propiolate → HCID 178469885, compound

HRID 2298421Notes

Reaction equation

HRID 2298421 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6](=[N:8]O)[NH2:7].[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[C:16]#[CH:17]>CO>[CH2:20]([O:19][C:15]([C:16]1[N:7]=[C:6]([C:5]2[CH:10]=[CH:11][CH:12]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=2)[NH:8][CH:17]=1)=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 609330N'-hydroxy-3-(trifluoromethyl)benzimidamide

Product 1

HCID 178469885HCID 178469885, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 3-trifluoromethylbenzamidoxime (19.89 g, 0.0974 mol) and ethyl propiolate (9.60 g, 0.0974 mol) in 100 mL methanol was refluxed overnight. The reaction was cooled and concentrated in vacuo and trace methanol removed by azeotroping with toluene (2×100 mL). The remaining residue was heated at 200° C. for 6 h in diphenyl ether (50 mL) before cooling and diluting with cold methanol (200 mL). The solid precipitate was filtered off and sucked dry on a glass frit to give 6.2 g of the title compound as a solid.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated in vacuo
  4. customremoved
  5. customby azeotroping with toluene (2×100 mL)
  6. temperaturebefore cooling
  7. additiondiluting with cold methanol (200 mL)
  8. filtrationThe solid precipitate was filtered off
  9. customsucked dry on a glass frit

Sources & evidence

ORD record
ord-895b0406ccad4cae83666b5bfe7fb978
Source dataset
uspto-grants-2002_12
Patent number
US06492516B1

Reaction notes

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