Tetrahydrofuran → HCID 14624421, compound

HRID 1650772Notes

Reaction equation

HRID 1650772 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]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18].[N:24]#[C:25][NH2:26].O1CCCC1.C(N(CC)CC)C>O>[NH2:26][C:25]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]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[N:24]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 9864CyanamideHCID 86743924HCID 86743924, compound

Product 1

HCID 14624421HCID 14624421, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20.5 g (0.05 mol) of pentafluoropropionyl chloride 2,6-dichloro-4-trifluoromethylphenylhydrazone and 2.5 g (0.06 mol) of cyanamide were added to 50 ml of tetrahydrofuran, and 6.1 g (0.06 mol) of triethylamine was dropwise added thereto under reflux and stirring. After completion of the dropwise addition, the mixture was stirred at the same temperature for 1 hour to complete the reaction. After cooling, the reaction solution was poured into water, and the precipitate was extracted with ethyl acetate. 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 12.5 g (yield: 60.1%) of the desired compound as white powder. Melting point: 181°-183° C.

Workup

  1. additionwas dropwise added
  2. temperatureunder reflux
  3. additionAfter completion of the dropwise addition
  4. stirringthe mixture was stirred at the same temperature for 1 hour
  5. customthe reaction
  6. temperatureAfter cooling
  7. extractionthe precipitate was extracted with ethyl acetate
  8. washThe organic layer was washed with water
  9. customdried
  10. distillationThen, the solvent was distilled off under reduced pressure
  11. washthe residue was washed with n-hexane

Sources & evidence

ORD record
ord-c292925ddba442bc89e6b259dbde1711
Source dataset
uspto-grants-1990_05
Patent number
US04925864

Reaction notes

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