Aminopyrazine → (2-Methoxy-5-nitrophenyl)-3-pyrazin-2-yl-urea

HRID 1821725Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1821725
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]=[C:13]=[O:14].[NH2:15][C:16]1[CH:21]=[N:20][CH:19]=[CH:18][N:17]=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[NH:12][C:13]([NH:15][C:16]1[CH:21]=[N:20][CH:19]=[CH:18][N:17]=1)=[O:14]

Komponenten

4

Edukt 2

HCID 78747AminopyrazineHCID 41675852-Methoxy-5-nitrophenyl isocyanate

Produkt 1

HCID 22046329(2-Methoxy-5-nitrophenyl)-3-pyrazin-2-yl-urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2-methoxy-5-nitrophenyl isocyanate (5.0 g, 25 mmol) and aminopyrazine (2.5 g, 26 mmol) in tetrahydrofuran (THF, 250 mL) was stirred at reflux for 24 hours. The product was precipitated from the cooled reaction mixture and was collected by filtration, washed with ethyl acetate, and dried in vacuo (4.3 g, 57%). 1H NMR (300 MHz, d6-DMSO) (mixture of rotamers) δ: 10.38 (br, s, 1H), 10.27 (s, 1H), 9.39, 8.88 (2 singlets, 1H), 9.10 (d, 1H), 8.33 (s, 1H), 8.26 (d, 1H), 7.98-8.25 (m, 1H), 7.97-7.84 (m, 1H), 4.05, 4.03 (2 singlets, 77:28 ratio, 3H).

Aufarbeitung

  1. temperatureat reflux for 24 hours
  2. customThe product was precipitated from the cooled reaction mixture
  3. filtrationwas collected by filtration
  4. washwashed with ethyl acetate
  5. customdried in vacuo (4.3 g, 57%)

Quellen und Nachweise

ORD-Eintrag
ord-c703c8b5b601473fa286eee703c64f2b
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608618B2

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