Dimethylformamide dimethyl acetal → Ethyl 1-(2,4-difluorophenyl)-7-ethylthio-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 232475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 232475
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:23]=[C:22]([S:24][CH2:25][CH3:26])[C:21]([F:27])=[CH:20][C:11]=1[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13].[CH3:28]OC(OC)N(C)C>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:10]2[C:11](=[CH:20][C:21]([F:27])=[C:22]([S:24][CH2:25][CH3:26])[N:23]=2)[C:12](=[O:13])[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:28]1

Komponenten

4

Edukt 2

HCID 78373Dimethylformamide dimethyl acetalHCID 13849319Ethyl 2-[2-(2,4-difluorophenylamino)-6-ethylthio-5-fluoronicotinoyl]acetate

Produkt 1

HCID 13849337Ethyl 1-(2,4-difluorophenyl)-7-ethylthio-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylateAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

In 3 ml of benzene was dissolved 160 mg of ethyl 2-[2-(2,4-difluorophenylamino)-6-ethylthio-5-fluoronicotinoyl]acetate, and 72 mg of N,N-dimethylformamide dimethylacetal was added thereto, after which the resulting mixture was subjected to reaction under reflux for 2.5 hours. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene-ethyl acetate (10:1 by volume)] to obtain 115 mg (yield 70.1%) of ethyl 1-(2,4-difluorophenyl)-7-ethylthio-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate having a melting point of 169.5°-171° C.

Aufarbeitung

  1. additionwas added
  2. customafter which the resulting mixture was subjected to reaction
  3. temperatureunder reflux for 2.5 hours
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe residue thus obtained
  6. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene-ethyl acetate (10:1 by volume)]

Quellen und Nachweise

ORD-Eintrag
ord-e64796bc230e4f0a86591f36a2e65ee5
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04851535

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