Succinyl chlorides

C14H30CI2N2O4. White powder prepared from dimethylaminoethanol and succinyl chloride, followed by methylation. Neuromuscular blocking agent used to relax skeletal muscles during certain types of surgical operation. 

The lowest members of the series of perfluoroalkanedicarboxyhc acids have been prepared and are stable compounds. They have been synthesized by oxidation of the appropriate chlorofluoroolefin as well as by electrochemical fluorination and direct fluorination. Perfluoromalonic acid is an oxidation product of CH2=CHCE2CH=CH2 (21). Perfluorosuccinic acid has been produced by oxidation of the appropriate olefin (see eq. 7) (5) or by electrochemical fluorination of succinyl chloride or butyrolactone (41) and subsequent hydrolysis. 

Succinyl chloride [543-20-4] is obtained from phosphorous pentachloride and succinic acid, from thionyl chloride and succinic acid or anhydride (91,92), or from phosgene and succinic anhydride (93). 

Succinic acid reacts with urea in aqeous solution to give a 2 1 compound having mp 141°C (116,117), which has low solubiUty in water. A method for the recovery of succinic acid from the wastes from adipic acid manufacture is based on this reaction (118,119). The monoamide succinamic acid [638-32-4] NH2COCH2CH2COOH, is obtained from ammonia and the anhydride or by partial hydrolysis of succinknide. The diamide succinamide [110-14-3], (CH2C0NH2)2, nip 268—270°C, is obtained from succinyl chloride and ammonia or by partial hydrolysis of succinonitrile. Heating succinknide with a primary amine gives A/-alkylsucckiknides (eq. 9). 

Dicarboxylic acid dichlorides with less than seven carbon atoms do not react to give tetraketones similar to 117, but instead undergo an intramolecular acylation (72) to give on hydrolysis the vinylogous acid anhydride (118), e.g., from succinyl chloride and the enamine (113). 

The acylation of enamino ketones can take place on oxygen or on carbon. While reaction at nitrogen is a possibility, the N-acylated products are themselves acylating agents, and further reaction normally takes place. The first reported acylation of enamino ketones (72) was that of 129, prepared by acylation of the enamine (113), which was shown to have undergone O acylation because on mild hydrolysis the enol ester (130) could be isolated. A similar reaction took place with other aliphatic acid chlorides (80) and with dibasic acid chlorides [e.g., with succinyl chloride to give 118 above]. 

Sanna reported that l,3-di(3-indolyl)-l,3-dioxo-%-propanc (266) and l,4-di(3-indolyl)-l,4-dioxo-M-butane (267) were formed by the action of malonyl chloride and succinyl chloride, respectively, on the indole Grignard reagent in ether, and analogous products could be obtained from 2-methylindole. 

Methyl succinyl chloride, ml95 Methylsulfonic acid, m34 Methyl theobromine, cl... 

Succinoglycans, 20 576-577 Succinonitrile, 8 174 Succinyl chloride, 23 420 Succinyl coenzyme A... 

Acetylcyclopentane-l,3-dione has been obtained in small amounts from the aluminum chloride-catalyzed reactions of vinyl acetate and succinyl chloride in 1,1,2,2-tetrachloro-ethane. 2-Acetylcyclopentane-l,3-diones have been prepared via Dieckmann condensation of 1,4-bisethoxycarbonylhexane-3,5-diones. The present procedure is essentially that of Mer nyi and Nilsson with some modifications. 

Acylation of 186 with an oc-substituted ethyl succinyl chloride generates the expected 4-acyl-5(4//)-oxazolones 187 that serve as precursors to ketomethylene and dehydro ketomethylene pseudodipeptides (Scheme 7.56). ... 

The above procedure is a modification of that described by Rasinski.2 Diphenyl succinate has also been prepared by the reaction of phenol and succinic acid in the presence of phosphorus pentoxide in toluene8 and by the treatment of phenol with succinyl chloride.4... 

N 14.68%, crysts (from MeOH), mp 85—85.6° sp gr 1.51. It was prepd by the Al chloride. catalyzed esterification of 2,2-dinitropropanol with succinyl chloride in methylene chloride soln (Refs 3 Sc 6). It is an insensitive compd (50% Impact Sensitivity, 2.5kg wt >320cm),... 

Tetrone (540) rearranges to /V,/V -bis sued nimide (541) either on heating or on reaction with succinyl chloride or hydrogen chloride in dioxane (63JA3052,67JA4875). 

Comparing with Reaction XX. (a) it will be seen that phthalyl chloride is tautomeric. Succinyl chloride is also considered to be similarly tautomeric, a number of facts supporting this view. Unlike phthalyl chloride, however, it reacts in the symmetrical form. 

Succinic Acid-Bis- [3-Nitryloxy-2,2-Bis-Nitryloxy-methyl-Propyl Ester]. C14H2oN6022 mw 624.40 N 37.46% OB to C02 -41.0% mp 88-90°. Prepn is by warming succinyl chloride with 0,0, 0 -PentaerythritoI Trinitrate in py. Its expl properties were not investigated (Ref 1, (1920))... 

The structure for homaline (114) was confirmed by a synthesis of bisdihydrodioxohomaline. The diazacyclooctane (118) was reacted with succinyl chloride and the bisamide reduced with LAH. The product 114 was identical with that prepared from homaline (93). 

Succinic anhydride has been obtained by distillation of succinic acid with phosphorus pentachloride, or from benzoyl chloride and sodium succinate.1 It has been prepared from succinic acid and phosphorus oxychloride or phosphorus pentachloride 2 by distillation of succinic acid with phosphorus pent-oxide 3 from acetyl chloride and barium succinate, or from suc-cinyl chloride and sodium acetate 4 from ethyl succinate and benzoyl chloride 5 from succinic acid and acetyl chloride, or from succinyl chloride and oxalic acid 6 from succinic acid and suc-cinyl chloride from succinic acid and acetic anhydride 7 from succinic acid and acetyl chloride 8 and from sodium succinate and acetic anhydride.9... 

Several dibasic acid halides are best prepared by this method from the readily available anhydrides. Thionyl chloride in the presence of a small amount of zinc chloride converts succinic and phthalic anhydrides to succinyl chloride (74%) and phthalyl chloride (86%), respectively. Phosphorus halides are used in similar preparations of phthalyl bromide (83%) and diphenic acid chloride (71%). ... 

Acid chlorides have proved to be mainly of value for the preparation of di(purin-8-yl)alkanes. Thus succinyl chloride with 4,5-diamino-6-oxo-l,6-dihydropyrimidine furnished a diamide which after cyclization gave a bispurine (Scheme 80) (61JOC1914). 

Acid Chlorides.— As succinic acid is a di-basic acid it forms a di-chloride when the acid, or the anhydride, is treated with phosphorus penta-chloride, PCI5. Two compounds result, however one, which is formed in much smaller amount, has been shown to be analogous to the chloride of malonic acid, malonyl chloride. It is known as the symmetrical succinyl chloride. 

This symmetrical succinyl chloride is a crystalline compound which melts at 190°. By far the greater part of the product of the action of phosphorus penta-chloride upon succinic acid is not the compound above mentioned but another to which an unsymmetrical formula has been given, as follows ... 

If, however, the di-amide is prepared by treating the di-chloride with ammonia another compound is obtained. As just stated, when the di-chloride is prepared the product is a mixture of two compounds, viz., the symmetrical and the unsymmetrical succinyl chlorides. This mixture of di-chlorides yields, by treatment with ammonia, a similar mixture of the symmetrical succinamide, just described, and another compound which is non-crystalline and which melts at 90°. To this latter compound the unsymmetrical structure has been given... 

It will be recalled that in the case of succinyl chloride both of these forms are obtained, but mostly the symmetrical (p. 282). Now from phthalic anhydride only one phthalyl chloride is obtained. This chloride acts like the unsymmetrical succinyl chloride, not like the symmetrical. The positive proof, however, that phthalyl chloride is the unsymmetrical compound is the following Sodium amalgam reduces phthalyl chloride by replacement of the chlorine with hydrogen. The compound formed is known as phthalide. This phthalide takes up water as anhydrides do and the product is hydroxy-methyl benzoic acid. 

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