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Hydrochloric Acid → 5-Ethyl 3-methyl 6-(difluoromethyl)-4-(isopropylamino)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

HRID 255434
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 255434
[F:1][CH:2]([F:25])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([O:15][CH3:16])=[O:14])=[C:5]([NH:17][CH:18]([CH3:20])[CH3:19])[C:4]=1[C:21]([O:23][CH3:24])=[O:22].[OH-].[K+].Cl.[C:29]([O-])([O-])=O.[K+].[K+].C(I)C>CN(C=O)C.O>[F:25][CH:2]([F:1])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[C:6]([C:13]([O:15][CH3:16])=[O:14])=[C:5]([NH:17][CH:18]([CH3:20])[CH3:19])[C:4]=1[C:21]([O:23][CH2:24][CH3:29])=[O:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 14013774Dimethyl 6-(difluoromethyl)-4-(iso propylamino)-2-(trifluoromethyl)-3,5-pyridine-dicarboxylate

Produkt 1

HCID 14013820
5-Ethyl 3-methyl 6-(difluoromethyl)-4-(isopropylamino)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate
Ausbeute 775,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel3×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4.1 g (0.001 mol) of product of Example 76, 0.62 g (0.011 mol) of KOH and 5 ml of H2O overnight. The reaction mixture was poured into 250 ml of H2O containing 50 ml of concentrated HCl, extracted with ether, dried (mgSO4) and concentrated in vacuo to 3.76 g of yellow air. This oil, 152 g (0.011 mol) of K2CO3 and 0.88 ml (0.011 mol) of ethyl iodide in 30 ml of DMF was stirred at room temperature overnight. The reaction mixture was poured into water extracted with ether, drid (MgSO4) and concentrated in vacuo to 3.64 g of yellow oil. Kugelrohr distillation at 53 Pa, pot temperature 103° C., afforded 2.98 g (70.5%) of product sa a light yellow oil which solidified; mp 37°-39° C.

Aufarbeitung

  1. extractionextracted with ether
  2. customdried (mgSO4)
  3. concentrationconcentrated in vacuo to 3.76 g of yellow air
  4. extractionextracted with ether
  5. concentrationconcentrated in vacuo to 3.64 g of yellow oil
  6. distillationKugelrohr distillation at 53 Pa, pot temperature 103° C.

Quellen und Nachweise

ORD-Eintrag
ord-4c69d8c06b17479a8ddebe5a4d38deab
Quelldatensatz
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04698093

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