Benzene, l-Chloro-2,4-dinitro

Dissolve 1.0g (or 1.0ml) of the amine and l.Og of l-chloro-2,4-dinitro-benzene in 5-10 ml of ethanol, add a slight excess of anhydrous potassium carbonate or of powdered fused sodium acetate, reflux the mixture on a water bath for 20-30 minutes and then pour into water. Wash the precipitated solid with dilute sodium carbonate solution, followed by dilute hydrochloric acid. Recrystallise from ethanol, dilute ethanol or glacial acetic acid. 

SYNS l-CHLOOR-2,4-DINITROBENZEEN (DUTCH) l-CHLOR-2,4-DINITROBENZENE 4-CHLORO-13-DINITROBENZENE 6-CHLORO-l,3-DINITRO-BENZENE l-CHLORO-2,4-DINITROBENZOL (GERMAN) l-CLORO-2,4-DINITROBENZENE (ITALIAN) 2,4-DINITROCHLOROBENZENE 1,3-... 

In 2-substituted dinitrothiophenes, phenylsulfone and p-nitro-phenoxy groups both react faster than the chloro group with pyridine, i.e., in a reverse order with respect to l-substituted-2,4-dinitro-benzenes, although with both substrates the factors involved are small. 

Among other kinetic studies of picryl chloride and I-chloro-2,4 dinitro-benzene with bases the works should be mentioned of Parker and Read [112) and Zollinger and co-workers [113] which have shown a much higher reactivity of picryl chloride. The reactions are greatly influenced by solvent and in some instances l-chloro-2,4-dlnitrobenzeneisinore reactive than picryl cliloride [114). 

DinitTO-l,3-(diamino-N,N,N, N -tetra-methyl)-benzene, yel nds (from chlf + ale), mp 191° sol in chlf si sol in hot ale was prepd by heating l,3-dinitro-4,6-dichlorobenzene with dimethylaniline in ale or from 2,4-dinitro-5-chloro-N,N- iimethylani-line 8c NH(CH3)2 (Ref 2)... 

Derivation Condensation of 2,4-dinitro-l-chloro-benzene and p-aminophenol. 

The synthesis of butralin (dibutalin, 3) starts with 4-/-butylphenol, the nitration of which with a mixture of nitric acid and acetic acid gives 4-t-butyl-2,6-dinitrophenol in a good yield. The dinitrophcnol is reacted in dimethyl formamide solution with phosphorus oxychloride to give l-/-butyl-4-chloro-2,6-dinitro-benzene. The reaction of the latter with jec-butylamine gives butralin (Bishop el al.,... 

Thioxo-3,4-dihydro-l,2,4-triazin-5(2//)-ones (330) and 2,4-dinitro- or 2,4,6-trinitro-chloro-benzene (331) afford [l,2,4]triazino[3,2-6]benzothiazol-3-ones (333) or the 5-arylated intermediates (332), depending on the reaction temperature (Scheme 60) <88LA1089>. 

N,N -D ime thy 1-4,6-dinitro-m-pbenylenedia-mine, (02N)2CeH2(NH.CH3)2 yel ndls (from acet), mp >290° (dec) obtd with other products by warming 5-chloro-l,2,4-trinitro-benzene or 5 bromo- deriv with ca 4 moles of benzaldehyde-methylimide in MeOH (Refs 4 7)... 

Bull(Fr) [33 33, 1175 St 11790905) 2,4-Dinitrodiphenylamine, (02N)2C6H3.NH.C6Hb red ndls (from benz), mp 157° sol in acet, chlf St hot ale can be prepd by interaction of 4-chloro-l,3 dinitro-benzene and aniline or by other methods (Refs 1-4)... 

Scheme 4.74 Synthesis imidazo[l,2-a]quinoxaline Af-oxides by interaction of l,3-dinitro-4-fluoro (and chloro)benzenes with cyclic amidines...

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