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1,2-Dichloroethane → N,N-diethyl-2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzamide

HRID 439545
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 439545
ClCCCl.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:16]=2[C:17](O)=[O:18])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].S(Cl)(Cl)=O.[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33]>O1CCCC1.CN(C)C=O>[CH2:32]([N:34]([CH2:35][CH3:36])[C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:26])[F:25])=[CH:23][C:15]=1[C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH3:5])[CH:8]=1)[CH3:33]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 157662622-(3,4-Dimethoxyphenyl)-4-(trifluoromethyl)benzoic acid

Produkt 1

HCID 11068964N,N-diethyl-2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzamideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

500 ml of 1,2-dichloroethane, 60 g (0.184 mol) of 2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzoic acid and 5 ml of N,N-dimethylformamide are introduced successively into a 1000 ml round-bottomed flask. 20 ml of thionyl chloride (0.276 mol) are then run in dropwise with stirring and while cooling at 0° C. When the addition is finished, the reaction mixture is heated progressively to 55° C. over 2 hours and then evaporated to dryness. The residue is taken up in 200 ml of tetrahydrofuran and then poured dropwise into a solution containing 58 ml (0.55 mol) of diethylamine in 200 ml of tetrahydrofuran maintained at a temperature below 10° C. When the addition is finished, the reaction mixture is stirred at room temperature for one hour and then evaporated to dryness. The residue is taken up in dichloromethane and washed successively with 1N HCl and distilled water. After drying over magnesium sulfate, the organic phase is evaporated under reduced pressure to provide 62.3 g (yield: 89%) of N,N-diethyl-2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzamide in the form of a white solid melting at 109°-110° C.

Aufarbeitung

  1. additionWhen the addition
  2. temperaturethe reaction mixture is heated progressively to 55° C. over 2 hours
  3. customevaporated to dryness
  4. additionpoured dropwise into a solution
  5. temperaturemaintained at a temperature below 10° C
  6. additionWhen the addition
  7. stirringthe reaction mixture is stirred at room temperature for one hour
  8. customevaporated to dryness
  9. washwashed successively with 1N HCl
  10. distillationdistilled water
  11. dry with materialAfter drying over magnesium sulfate
  12. customthe organic phase is evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c7400e61c378451182452ad5e15faa66
Quelldatensatz
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05514719

Notizen zur Reaktion

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