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Hexane → 2-(2,4-Difluorophenylamino)-5-fluoro-6-methoxynicotinoyl chloride

HRID 246938
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 246938
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:18]=[C:17]([O:19][CH3:20])[C:16]([F:21])=[CH:15][C:11]=1[C:12](O)=[O:13].S(Cl)([Cl:24])=O.CCCCCC>C(Cl)Cl.CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:18]=[C:17]([O:19][CH3:20])[C:16]([F:21])=[CH:15][C:11]=1[C:12]([Cl:24])=[O:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8058HexaneHCID 24386Thionyl ChlorideHCID 138217673-Pyridinecarboxylic acid,2-[(2,4-difluorophenyl)amino]-5-fluoro-6-methoxy-

Produkt 1

HCID 138493482-(2,4-Difluorophenylamino)-5-fluoro-6-methoxynicotinoyl chlorideAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysator
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In 150 ml of methylene chloride was suspended 5.00 g of 2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinic acid, and 5.98 g of thionyl chloride and 3 drops of N,N-dimethylformamide was added thereto, after which the resulting mixture was subjected to reaction under reflux for 2 hours. The solvent and the excessive thionyl chloride were removed by distillation under reduced pressure, and to the crystalline material thus obtained was added 10 ml of n-hexane, after which crystals were collected by filtration to obtain 4.87 g (yield 91.7%) of 2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinoyl chloride having a melting point of 153°-154° C.

Aufarbeitung

  1. additionwas added
  2. customafter which the resulting mixture was subjected to reaction
  3. temperatureunder reflux for 2 hours
  4. customThe solvent and the excessive thionyl chloride were removed by distillation under reduced pressure
  5. customto the crystalline material thus obtained
  6. filtrationafter which crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-dc35bf0568314895b61c2638f292a446
Quelldatensatz
uspto-grants-1987_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04704459

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