Pyridine → 4'-Chloro-2'-fluoro-5'-[hexahydro-2,4,6trioxo-3(2-propynyl)-s-triazin-1-yl]acetanilide

HRID 52426

Reaktionsgleichung

Reaktionsgleichung von HRID 52426
[C:1]([NH:4][C:5]1[C:6]([F:19])=[CH:7][C:8]([Cl:18])=[C:9]([NH:11][C:12]([NH:14][CH2:15][C:16]#[CH:17])=[O:13])[CH:10]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.[C:26](=[O:31])=[N:27][C:28](Cl)=[O:29]>C(Cl)Cl>[Cl:18][C:8]1[C:9]([N:11]2[C:28](=[O:29])[NH:27][C:26](=[O:31])[N:14]([CH2:15][C:16]#[CH:17])[C:12]2=[O:13])=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[C:6]([F:19])[CH:7]=1

Komponenten

5

Edukt 3

HCID 1049Pyridine2×HCID 119708Isocyanatocarbonyl chloride2×HCID 538737111-(5-Acetamido-2-chloro-4-fluorophenyl)-3-(2-propynyl)urea

Produkt 1

HCID 569836604'-Chloro-2'-fluoro-5'-[hexahydro-2,4,6trioxo-3(2-propynyl)-s-triazin-1-yl]acetanilide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1-(5-acetamido-2-chloro-4-fluorophenyl)-3-(2-propynyl)urea (4.50 g, 15.9 mmol), and pyridine (2.56 mL, 31.8 mmol) in methylene chloride is treated with N-(chlorocarbonyl) isocyanate (1.92 mL, 23.9 mmol), stirred at room temperature overnight, refluxed for 90 minutes, cooled to room temperature, treated with additional pyridine (1.30 mL) and N-(chlorocarbonyl) isocyanate (1.92 mL), stirred for 10 minutes, cooled to room temperature, and filtered to obtain a solid. The solid is washed sequentially with water and hexanes, and dried to give the title product as a tan solid.

Aufarbeitung

  1. temperaturerefluxed for 90 minutes
  2. temperaturecooled to room temperature
  3. stirringstirred for 10 minutes
  4. temperaturecooled to room temperature
  5. filtrationfiltered
  6. customto obtain a solid
  7. washThe solid is washed sequentially with water and hexanes
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fca0e40b9f674b368b605110c1fc8a8b
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616706

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