Dimethylformamide → 5-Chloro-2,4-dinitrobenzamide
Reaktionsgleichung
[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([Cl:16])=[CH:9][C:5]=1[C:6](O)=[O:7])([O-:3])=[O:2].C[N:18](C=O)C.[OH-].[NH4+]>S(Cl)(Cl)=O.CC(C)=O>[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([Cl:16])=[CH:9][C:5]=1[C:6]([NH2:18])=[O:7])([O-:3])=[O:2]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
2,4-Dinitro-5-chlorobenzoic acid (7.00 g, 28.4 mmol) was suspended in 40 mL thionyl chloride containing 3 drops of DMF. The suspension was warmed to reflux for four hours. After cooling to room temperature, solvent was removed by rotary evaporation leaving a golden yellow liquid. This was diluted with 30 mL acetone and added dropwise over 20 minutes to a 0° C. solution of 20 mL concentrated ammonium hydroxide. The reaction was stirred at 0° C. for 30 minutes, then poured into 250 g of ice. The yellow orange precipitate was collected by filtration and washed well with water. The solid was dried first by water aspirator then under high vacuum to furnish 5.9 g (24 mmol, 84% yield) of product. NMR (400 MHz; acetone-d6): δ 8.75, s 1H, 8.25, s 1H; mp 201-203° C.
Aufarbeitung
- temperatureThe suspension was warmed
- temperatureto reflux for four hours
- customsolvent was removed by rotary evaporation
- customleaving a golden yellow liquid
- filtrationThe yellow orange precipitate was collected by filtration
- washwashed well with water
- dry with materialThe solid was dried first by water aspirator then under high vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-cb1a0236540d47a7867bff0c669ea6a6
- Quelldatensatz
- uspto-grants-2000_07
- Patentnummer
- US06087368
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