Triethylamine → HCID 14624495, compound

HRID 1032349Notes

Reaction equation

HRID 1032349 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:25][C:26]#[N:27])[CH3:24].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:26]([NH:25][CH2:23][CH3:24])=[N:27][C:15]([CH:16]([C:18]([F:21])([F:20])[F:19])[CH3:17])=[N:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1221111038434-78-5HCID 86744217HCID 86744217, compound

Product 1

HCID 14624495HCID 14624495, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.8 g (0.02 mol) of 2-trifluoromethylpropionyl chloride 2,6-dichloro-4-trifluoromethylphenylhydrazone and 1.5 g (0.022 mol) of ethyl cyanamide were dissolved in 50 ml of tetrahydrofuran, and 2.5 g (0.025 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 3 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 5.8 g (yield: 69%) of the desired compound having a melting point of from 82° to 83° C. as slightly yellow 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-2b499217ecfa43849b8c087b98708ed6
Source dataset
uspto-grants-1990_09
Patent number
US04957935

Reaction notes

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