Methyl iodide → 2(3H)-benzoxazolone, 3-methyl-5-nitro-
Reaktionsgleichung
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[O:12])[NH:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:16]I>CN(C=O)C>[CH3:16][N:9]1[C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[O:11][C:10]1=[O:12]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A solution of 5-nitro-3H-benzooxazol-2-one (26 g) in DMF (100 mL) was added to a suspension of NaH (60% in mineral oil, 10.71 g) in DMF (100 mL) over a period of 1 hour. Stirring was continued for 45 minutes at r.t. The mixture was cooled to 0° C. and methyl iodide dissolved in DMF (20 mL) was added dropwise over a period of 30 minutes. The mixture was stirred over night at r.t. The reaction mixture was poured into ice/water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. CH2Cl2:methanol=4:1 (150 mL) was added to the resulting precipitate and the suspension was stirred for 1 hour at r.t. The solid was filtered off and dried in vacuo. The title compound was obtained as a orange solid (18.33 g, 62%). MS (EI)=194.0 [M+].
Aufarbeitung
- additionwas added dropwise over a period of 30 minutes
- stirringThe mixture was stirred over night at r.t
- extractionextracted two times with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customthe solvent was evaporated
- additionCH2Cl2:methanol=4:1 (150 mL) was added to the resulting precipitate
- stirringthe suspension was stirred for 1 hour at r.t
- filtrationThe solid was filtered off
- customdried in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-78fc961df5ff4971b66cf61d053b455c
- Quelldatensatz
- uspto-grants-2012_09
- Patentnummer
- US08268820B2
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