1,1'-Carbonyldiimidazole → Ethyl 2-amino-2-(4-trifluormethyl-3-pyridinecarbonyloxyimino)-acetate

HRID 47216

Reaktionsgleichung

Reaktionsgleichung von HRID 47216
[C:1]([N:8]1C=CN=C1)([N:3]1C=CN=C1)=O.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[C:21]([OH:23])=[O:22].[CH2:26]([O:28][C:29](NC=NO)=[O:30])[CH3:27]>O1CCOCC1>[NH2:8][C:1](=[N:3][O:22][C:21]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:15]=1[C:14]([F:13])([F:24])[F:25])=[O:23])[C:29]([O:28][CH2:26][CH3:27])=[O:30]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-HCID 136108985Ethoxycarbonylformamide oxime

Produkt 1

HCID 73994277Ethyl 2-amino-2-(4-trifluormethyl-3-pyridinecarbonyloxyimino)-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

17.3 g of carbonyldiimidazole are initially charged in 200 ml of 1,4-dioxane and, a little at a time, admixed with 20 g of 4-trifluoromethyl-3-pyridinecarboxylic acid. The mixture is stirred at room temperature for 1 h and subsequently heated to 45° C. for 2 h. After cooling to 30° C., 14.5 g of ethoxycarbonylformamide oxime are added and the mixture is stirred at 45° C. for 3 h. The precipitated solid is filtered off with suction and the filtrate is concentrated to 50 ml and, together with the solid, added to 250 ml of ice-water. The solid is filtered off with suction and dried at 50° C. under reduced pressure. This gives 28.7 g of the product as a white solid of mp. 172-174° C.

Aufarbeitung

  1. temperaturesubsequently heated to 45° C. for 2 h
  2. temperatureAfter cooling to 30° C.
  3. stirringthe mixture is stirred at 45° C. for 3 h
  4. filtrationThe precipitated solid is filtered off with suction
  5. concentrationthe filtrate is concentrated to 50 ml and, together with the solid
  6. additionadded to 250 ml of ice-water
  7. filtrationThe solid is filtered off with suction
  8. customdried at 50° C. under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ec1791fae4614b48a0fc36d4132dde9f
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699853B2

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