Water → 5-(4-benzyloxycarbonylaminophenyl)-3-methyl-2(1H)-pyrazinone

HRID 542446

Reaktionsgleichung

Reaktionsgleichung von HRID 542446
[H-].[Na+].O[N:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:22]1[C:27]([CH3:28])=[N:26][CH:25]=[CH:24][N:23]=1.[OH2:29]>CN(C)C=O>[CH2:7]([O:6][C:5]([NH:4][C:15]1[CH:20]=[CH:19][C:18]([C:25]2[N:26]=[C:27]([CH3:28])[C:22](=[O:29])[NH:23][CH:24]=2)=[CH:17][CH:16]=1)=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 66769Pyrazine, 2-chloro-3-methyl-HCID 12358018benzyl N-hydroxy-N-phenylcarbamate

Produkt 1

HCID 138535615-(4-benzyloxycarbonylaminophenyl)-3-methyl-2(1H)-pyrazinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred suspension of sodium hydride (2.1 g, 50% in oil) in dry dimethylformamide (35 ml) with external cooling was added portionwise, benzyl N-hydroxy-N-phenylcarbamate (10.6 g). After 5 minutes a brown solution was obtained to which was added 2-chloro-3-methylpyrazine (5.5 g) and the mixture was allowed to attain room temperature. The solution was poured into water (200 ml) and the aqueous phase decanted from the dark oil. The aqueous solution deposited a yellow solid which was collected and washed with ethanol to give 5-(4-benzyloxycarbonylaminophenyl)-3-methyl-2(1H)-pyrazinone (1.55 g. m.p. 238°-240° C.).

Aufarbeitung

  1. temperaturewith external cooling
  2. additionwas added portionwise
  3. customAfter 5 minutes a brown solution was obtained to which
  4. customto attain room temperature
  5. customthe aqueous phase decanted from the dark oil
  6. customwas collected
  7. washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-e65a397730fd43d1962fdec053c20b38
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04657906

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