Acetic Anhydride → N-(5-nitropyrimidin-2-yl)acetamide

HRID 253698

Reaktionsgleichung

Reaktionsgleichung von HRID 253698
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>C1(C)C=CC=CC=1>[N+:8]([C:5]1[CH:4]=[N:3][C:2]([NH:1][C:11](=[O:13])[CH3:12])=[N:7][CH:6]=1)([O-:10])=[O:9]

Komponenten

4

Edukt 2

HCID 7918Acetic Anhydride2×HCID 764905-Nitropyrimidin-2-amine

Produkt 1

HCID 45071770N-(5-nitropyrimidin-2-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To 2-amino-5-nitropyrimidine (0.42 g, 3.0 mmol) dissolved in toluene (2 ml) was added acetic anhydride (1.4 ml, 15 mmol). The reaction mixture was stirred at 90° C. for 15 hr, after which an additional amount of acetic anhydride was added (0.7 mL) and the mixture was stirred at reflux for another 16 h. The solvent was removed in vacuo and to the residue was added hexane (10 mL) and DCM (1 mL). The solid was collected by filtration, dried to give N-(5-nitropyrimidin-2-yl)acetamide as an off-white solid. MS (ESI, pos. ion) m/z: 183 (M+1).

Aufarbeitung

  1. stirringthe mixture was stirred
  2. temperatureat reflux for another 16 h
  3. customThe solvent was removed in vacuo and to the residue
  4. additionwas added hexane (10 mL) and DCM (1 mL)
  5. filtrationThe solid was collected by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e0baeb2ebcfd484482e11216a87fde25
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872128B2

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