Triethylamine → HCID 14624496, compound

HRID 1032350Notes

Reaction equation

HRID 1032350 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][N:14]=[C:15](Cl)[CH:16]([C:18]([F:21])([F:20])[F:19])[CH3:17].[CH2:23]([NH:26][C:27]#[N:28])[CH2:24][CH3:25].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:27]([NH:26][CH2:23][CH2:24][CH3:25])=[N:28][C:15]([CH:16]([C:18]([F:21])([F:20])[F:19])[CH3:17])=[N:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12556863HCID 12556863, compoundHCID 86744217HCID 86744217, compound

Product 1

HCID 14624496HCID 14624496, compoundYield 700.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.8 g (0.02 mol) of 2-trifluoromethylpropionyl chloride 2,6-dichloro-4-trifluoromethylphenylhydrazone and 1.9 g (0.002 mol) of propyl cyanamide were dissolved in 50 ml of tetrahydrofuran, and 2.6 g (0.026 mol) of triethylamine was dropwise added thereto under stirring and cooling with ice. After completion of the dropwise addition, the stirring was continued at room temperature for 2 hours. The solvent was distilled off under reduced pressure. The residue was dissolved in hexane, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. Then, hexane was distilled off under reduced pressure. Further, the residue was subjected to distillation under reduced pressure. The fraction having a boiling point of 110°-120° C./0.1-0.2 mmHg was subjected to recrystallization from hexane to obtain 6.1 g (yield: 70%) of the desired compound having a melting point of from 73° to 74.5° C. as white prismatic crystals.

Workup

  1. temperaturecooling with ice
  2. additionAfter completion of the dropwise addition
  3. distillationThe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in hexane
  5. washthe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThen, hexane was distilled off under reduced pressure
  8. distillationFurther, the residue was subjected to distillation under reduced pressure
  9. customwas subjected to recrystallization from hexane

Sources & evidence

ORD record
ord-7465daa8f2e248b3922aadf6a5bf0140
Source dataset
uspto-grants-1990_09
Patent number
US04957935

Reaction notes

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