Tetrahydrofuran → HCID 15171054, compound

HRID 1650763Notes

Reaction equation

HRID 1650763 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)[C:16]([CH3:19])([CH3:18])[CH3:17].[N:21]#[C:22][NH2:23].O1CCCC1.C(N(CC)CC)C>O>[NH2:23][C:22]1[N:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][C:4]=2[Cl:12])[N:14]=[C:15]([C:16]([CH3:19])([CH3:18])[CH3:17])[N:21]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 9864CyanamideHCID 86743921HCID 86743921, compound

Product 1

HCID 15171054HCID 15171054, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7.0 g (0.02 mol) of 2,2-dimethylpropionyl chloride 2,6-dichloro-4-trifluoromethylphenylhydrazone and 1.7 g (0.04 mol) of cyanamide were added to 100 ml of tetrahydrofuran. Then, 4.0 g (0.04 mol) of triethylamine was dropwise added under reflux and stirring. After completion of the dropwise addition, the stirring was continued at the same temperature for further 1 hour. After cooling, the reaction solution was poured into water, and the precipitate was extracted with toluene. The organic layer was washed with water and dried. Then, the solvent was distilled off under reduced pressure, and the residue was washed with n-hexane to obtain 5.3 g (yield: 74.6%) of the desired compound as white prismatic crystals. The melting point: 208°-212° C.

Workup

  1. temperatureunder reflux
  2. additionAfter completion of the dropwise addition
  3. temperatureAfter cooling
  4. extractionthe precipitate was extracted with toluene
  5. washThe organic layer was washed with water
  6. customdried
  7. distillationThen, the solvent was distilled off under reduced pressure
  8. washthe residue was washed with n-hexane

Sources & evidence

ORD record
ord-f5b3b22fbe1d4a4fb252e9dc61efb124
Source dataset
uspto-grants-1990_05
Patent number
US04925864

Reaction notes

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