Tetrahydrofuran → HCID 14624364, Verbindung

HRID 1650773

Reaktionsgleichung

Reaktionsgleichung von HRID 1650773
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([Cl:13])[C:3]=1[NH:14][N:15]=[C:16](Cl)[C:17]([CH3:20])([CH3:19])[CH3:18].[CH2:22]([N:24]([CH2:27][CH3:28])[C:25]#[N:26])[CH3:23].O1CCCC1.C(N(CC)CC)C>O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([Cl:13])[C:3]=1[N:14]1[C:25]([N:24]([CH2:27][CH3:28])[CH2:22][CH3:23])=[N:26][C:16]([C:17]([CH3:20])([CH3:19])[CH3:18])=[N:15]1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 12050DiethylcyanamideHCID 86743925HCID 86743925, Verbindung

Produkt 1

HCID 14624364HCID 14624364, VerbindungAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

7.3 g (0.02 mol) of 2,2-dimethylpropionyl chloride 2,6-dichloro-4-trifluoromethoxyphenylhydrazone and 2.0 g (0.02 mol) of N,N-diethylcyanamide were added to 100 ml of tetrahydrofuran, and 2.2 g (0.02 mol) of triethylamine was dropwise added under reflux and stirring. After completion of the dropwise addition, the mixture was stirred at the same temperature for 0.5 hour. After cooling, the reaction solution was poured into water, and the precipitate was extracted with chloroform. The chloroform layer was washed with water and dried, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 7.4 g (yield: 87.1%) of the desired compound as a pale yellow liquid. Refractive index nD20 : 1.4940.

Aufarbeitung

  1. additionwas dropwise added
  2. temperatureunder reflux
  3. additionAfter completion of the dropwise addition
  4. stirringthe mixture was stirred at the same temperature for 0.5 hour
  5. temperatureAfter cooling
  6. extractionthe precipitate was extracted with chloroform
  7. washThe chloroform layer was washed with water
  8. customdried
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-eb05cccaa5ee4164ab241518e4b43c55
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04925864

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