Oxalic acid Amides

Fig. 19 Bola-type bis(amino add and amide) 122-124 and 127, bis(amino alcohol) 125, and meso-diastereomer 126 oxalic acid amide gelators...

The treatment of kasuganobiosamine with dimethyl ester of oxalic acid followed by concentrated aqueous ammonia gave two kinds of amides. The amide (11a) with pK a 7.6 was identical with the amide of kasugamycinic acid, which was prepared from kasugamycinic acid by treatment with anhydrous hydrogen chloride-methanol followed by concentrated aqueous ammonia. The other isomer (lib) with pK a 7.8, was named amide of isokasugamycinic acid. 

Treatment of D-glucoascorbic acid (XV) with diazomethane gives a 2,3-dimethyl derivative (LXXIX) and this upon repeated treatment with silver oxide and methyl iodide yields 2,3,5,6,7-pentamethyl-D-glucoascorbic acid (LXXX). Ozonization of the latter followed by hydrolysis gives oxalic acid and 3,4,5-trimethyI-D-arabonic acid (LXXXI). This acid was shown to possess a free hydroxyl group at C2 by reason of the fact that the amide of LXXXI gives a positive Weerman reaction for a-hydroxy amides, i.e., when the amide is treated with sodium hypochlorite, sodium isocyanate is produced, the latter being identified by... 

Diisopropenyl oxalate results from the addition of oxalic acid to propyne. The ester condenses with all types of amines under ruthenium catalysis to yield the corresponding ester amides or oxamides, depending on the amounts of amines used (equation 104)327. 

A variety of ketones 249 can be directly converted into the secondary amides 253 (the expected product of a Beckmann rearrangement of the corresponding oximes 250) in high yield, by heating them with hydroxylamine hydrochloride and anhydrous oxalic acid (equation 75). Aromatic aldehydes afforded mixtures of nitriles and amides. The... 

Aromatic 1,2-diamines (46) condense readily with 1,2-diketones, a-keto amides, a-keto acids, or oxalic acid and provide quantitative yields in the solid state. For example, benzils (338) react with o-phenylenediamines (46) at room temperature upon milling and drying (Scheme 54). All products 339 are also obtained with 100% yield by heating to the temperatures given after initial stoichiometric cogrinding. Similarly 340 and 46a (70 °C, 15 min) give quantitatively compound 341 [104]. 

In addition to the acid anhydride12,14,17-19 shown as the source of the carbon at C-5 in the final product [Eq. (1)], ketene,20 reactive acids such as formic21 and acrylic,22 acid chlorides,10,23-26 esters,27 ortho esters,28-34 ethyl oxalate,35 amides,35 and iminoethers36 [Eqs. (12-14)] may also furnish the C-5 carbon. 

IMIDES. An imide may be defined as a compound that has the divalent radical NH combined with two acid radicals. The definition implies that the acid from which an imide is derived must be a dibasic acid, such as oxalic acid, HOOC COOH. or succinic acid. HOOC CH2 CH COOH. The derivatives of these two acids illustrate the relationship between amides and imidcs. 

SYNS AMID KYSELINY STAVELOVE (CZECH) 1-CARBAMOYLFORMIMIDIC ACID ETHANEDIAMIDE OXALAMIDE OXALIC ACID DIAMIDE OXAMID (CZECH) OXAMIAODIC ACID... 

The two major techniques for the preparation of triazolecarboxylic acids are the ami-drazone method and transformations or replacements of existing functions. In the former case one can introduce the carboxylic acid through starting materials such as (323). Alternatively, cyclization of other amidrazones can be accomplished with derivatives of oxalic acid, e.g. by converting the acylamidrazone (324) into the amide (325) from which the acid may be liberated by hydrolysis. A particularly convenient method for the preparation of carboxylic acids, esters and amides is the rearrangement arylazooxazolinones (Scheme 117). 

Oxamide has been used as a stabilizer for NC prepns (Ref 6), as a coolant in proplnt formulations because the amt of smoke contributed by it was small (Ref 2), and as a component of Oxamide Explosive Composition (see below) The requirements of the US Armed Forces are detailed in Mil Spec Ml L-O-60863, Oxr amide (15 December 1967) as follows moisture content — 0.1% max purity — 99.0% min acidity (as oxalic acid) - 0.05% max pH — 6.5 1.5 residue on ignition — -.05% max particle size, grade A — 4 2 microns granulation, grade B — thru US Standard Sieve No 30, 100% min thru US Standard Sieve No 325,... 

Esters, Acid Chlorides, Acid Amides.—Just as oxalic acid, because of its di-basic character, forms two series of salts, it also forms two series of the other acid derivatives, viz., estersy acid chlorides and acid amides. 

The amides of oxalic acid are also best prepared by the action of ammonia not upon the acid itself or the acid chloride but upon the esters. 

Acid Amides.—Succinic acid, like oxalic acid, forms both a mono-and a di-amide. 

Carbamic Acid.— It will be recalled that oxalic acid, the simplest dicarboxylic acid, yields a corresponding di-amide and that there is also formed an intermediate product known as oxamic acid. 

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