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Nicotinic Acid → N-[4-(3-Fluoronaphthalen-2-yl)-6-imino-1,6-dihydro-1,3,5-triazin-2-yl]pyridine-3-carboximidic acid

HRID 1981823
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1981823
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.CS(Cl)(=O)=O.[NH2:15][C:16]1[N:21]=[C:20]([NH2:22])[N:19]=[C:18]([C:23]2[C:24]([F:33])=[CH:25][C:26]3[C:31]([CH:32]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:17]=1>N1C=CC=CC=1>[NH2:22][C:20]1[N:21]=[C:16]([NH:15][C:1](=[O:9])[C:2]2[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=2)[N:17]=[C:18]([C:23]2[C:24]([F:33])=[CH:25][C:26]3[C:31]([CH:32]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:19]=1
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Komponenten

5

Edukt 3

HCID 938Nicotinic AcidHCID 31297Methanesulfonyl chlorideHCID 13373714HCID 13373714, Verbindung

Produkt 1

HCID 11971098N-[4-(3-Fluoronaphthalen-2-yl)-6-imino-1,6-dihydro-1,3,5-triazin-2-yl]pyridine-3-carboximidic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Nicotinic acid (0.58 gram) was dissolved in 10 ml of pyridine, 0.27 gram of methanesulfonyl chloride was added thereto, the mixture was heated to reflux for thirty minutes, 0.5 gram of 2,4-diamino-6-(2-fluoro-3-naphthyl)-s-triazine was added, and the mixture was heated to reflux for four hours. After the reaction was completed, pyridine was evaporated, water was added to the residue, the resulting separated mass was subjected to a column chromatography using 100 grams of silica gel, and eluted with ethyl acetate-benzene (9:1) to afford 2-amino-4-nicotinoylamino-6-(2-fluoro-3-naphthyl)-s-triazine, colourless crystals, melting point 230° to 235° C. (with decomposition). The yield was 0.35 gram.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for thirty minutes
  3. temperaturethe mixture was heated
  4. temperatureto reflux for four hours
  5. custompyridine was evaporated
  6. additionwater was added to the residue
  7. customthe resulting separated mass
  8. washeluted with ethyl acetate-benzene (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-98416a3d5add472a8321cc20d8314b48
Quelldatensatz
uspto-grants-1986_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04593025

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