N-Nitrourethans

The addition of N-nitrourethanes 429 to carbodiimides also afforts insertion products 430. ... 

N 36.83%, OB to C02 -42.1% colorless needles from ether nip 38° d 1.243 at 49/4° RI 1.4616 at 48,6°. V sol in cold w, ale, chlf and benz less sol in eth and still less sol in petr eth. Can be prepd by nitrating n-methyl-urethane with abs nitric acid. The resulting soln of methyl nitrourethane is drowned in w, neutralized with Na carbonate, and extrd with eth to remove methyl nitrourethane. On passing ammonia gas thru the eth extract, a white ppt of the ammonium salt of methylnitramine is deposited and sepd by filtration. It is disd in ale and boiled to drive off the ammonia, and... 

Diaminobiuret has been prepared only from N-tricarboxylic ester and hydrazine hydrate.1 Ethyl hydrazinecarboxylate has been prepared by reduction of nitrourethan electrolytically2 or with zinc dust and acetic acid,3 and by the action of hydrazine hydrate on diethyl carbonate,4 6 ethyl chlorocarbonate,6 and N-tricarboxylic ester.1... 

Ref Beil 4, 254, [693] 15321 NfN -Dinitro-NfN -dicarboethoxyethylenedi-amine 1,4-Dinitro-l,4-dicarboxy-1,4-diaza-butone or Ethylene-bis-nitrourethane (called N.N -Dinitro-N.N -dicarbathoxy-athylendiamin or N.N -Dinitro-athylendiurethan in Ger), C2H500C.N(N02).CH2.CH2.N(N02).C00C2H5 mw 294.22, N 19.04% fine ndls (from w), mp 83-84° sol in chlf benz si sol in ale almost insol in cold w prepd by nitrating ethylenediurethane with the strongest coned HNO3... 

W.C.Fernelius, ChemRevs 12, 67(1933) 20,413(1937) 3)Franklin(l935), 54-5 4)Inorg-Synth 1(1939) 74-7 2(1946), 128-35 Nitramide or Nitroxyl amide, 02N.NH2, raw 62.03, N 45.1755. Wh solid, mp 72-5° with de-compn puffs off on rapid heating. Sol in w (slowly dec) and in common solvents, except petr ether. Was first, prepd in 1890 by Mathieu-Plessy but not properly identified. Thiele Lachman prepd it in 1894(Refs 1,2 3) from nitrourethane,OaN.NHCOO.CaHs, and described its props. Since then nitramide was prepd by various investigators, mostly by hydrolysis and decarboxylation of potassium —N —... 

N02N(NH4)C02C2H6 Ammonium salt of nitrourethan, 1 69 N03H Nitric acid, 3 13 4 52 N(S03K)s Potassium nitridotri-sulfate, 2 182... 

A series of benzylnitramines were prepared by either nitration of the carbamates or N-alkylation of nitrourethane, followed by ammonolysis. These represent one-phenylnitramines, known broadleaf herbicides. Nastic responses and growth inhibition observed for this class suggested similarity to the auxin type herbicides. To determine if die preference for the (R) -configuration extended to nitramines, l-(2 6 -dichlorophenethyl)nitramine was resolved and the absolute configuration determined by asymmetric synthesis. A comparison of the (+) and (-) isomers in herbicidal and in vitro assays was performed and the results are discussed. 

Thiele discovered nitro- and amino-guanidine and described a preparation of hydrazine from aminoguanidine, also of hydrazoic acid from hydrazine, ethyl nitrite, and alkali, and at first independently proposed and adopted the correct linear formula N. N NH, which had been given by Angeli, but later reverted to Curtius s cyclic formula on the basis of misleading parachor results. Thiele and A. Lachman discovered nitramide by way of nitrourethane, C2H50-C0-NH-N02. They formulated it both as the amide, NH2 N02, or imide, NH NO OH, of nitric acid. Thiele later preferred the second formula. 

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