Chloro cyanogen

The distance C—Cl is also shortened in Cl—C=N chloro-cyanogen and Cl—C=C—H chloroacetylene, even to 1.67 A and 1.68 A, respectively. Quantitative calculations on the character of the C—Cl bond in substituted ethylene and benzene derivatives are in good agreement with the available experimental data (Ketelaar and Sherman). 

SYNS CHLORCY.W CHLORINE CYANIDE CHLOROCYAN CHLOROCYANIDE O CHLORO-CYANOGEN CHLORURE de CYANOGENE CYANOGEN CHLORIDE (ACGIH.OSHA) CY.ANOGEN... 

Additional pyrimido[4,5-f ]quinoline syntheses include one involving the action of cyanogen bromide on 2-chloro-3-cyanoquinoline similar to that described for pyridines (Section 2.15.5.5.1) (78JHC877), and a synthesis of pyrimido[4,5-fe]quinoline-2-carboxylic... 

Chloro-7-(2-fluorophenyl)-5/f-dibenz[c,e]azepine (54) has been prepared in a similar manner from 2-[2-(bromomethyl)phenyl)-5-chloro-2 -fluorodiphenyl ketone (53, X = Br),93 but can be obtained in a superior yield (85%) as the methanesulfonate salt by cleavage of the [(dimethylamino)methyl] derivative 53 (X = NMe2) with cyanogen bromide followed by treatment with ethanolic ammonia.94... 

Nicotinic acid and related compounds react with l-chloro-2,4-dinitrobenzene in the manner of the cyanogen bromide reaction to yield derivative I, which possibly also decarboxylates at elevated temperature. In alkaline medium this derivative first adds an hydroxyl ion and then undergoes ring opening to yield the colored derivative II. 

Butyraldehyde oxime, 1655 Carbon, Unsaturated oils, 0298 Chlorine, Carbon disulfide, 4047 f l-Chloro-2,3-epoxypropane, Contaminants, 1162 Cyanogen chloride, 0323... 

Cycloadditions to a cyano group are comparatively rare. The high-temperature reactions of 1,3-dienes, e.g. butadiene, isoprene and 2-chloro-l,3-butadiene, with dicyanogen, propionitrile or benzonitrile result in formation of pyridines (equation 80)70. Sulfonyl cyanides 147, obtained by the action of cyanogen chloride on sodium salts of sulfinic acids, add to dienes to give dihydropyridines 148, which are transformed into pyridines 149 by oxidation (equation 81)71. 

It was suggested that the chlorination of naphthalene in tap water accounted for the presence of chloro- and dichloronaphthalenes (Shiraishi et ah, 1985). Kanno et al. (1982) studied the aqueous reaction of naphthalene and other aromatic hydrocarbons (benzene, toluene, o-, m-, and p-xylene) with hypochlorous acid in the presence of ammonium ion. They reported that the aromatic ring was not chlorinated as expected but was cleaved by chloramine forming cyanogen chloride. The amount of cyanogen chloride increased at lower pHs (Kanno et ah, 1982). 

Treatment of cyanoimidates, easily obtained from cyanogen and alcohols in the presence of triethylamine, gave with sulfur monochloride the corresponding 4-chloro-l,2,5-thiadiazoles 36 in good-to-moderate yields (1967JOC2823, 1998JMC379 Scheme 20). 

Nitrobromoform, Bromoacquinite, Tribromonitromethane, Picfume bromide Chloroacetone, l-Chloro-2-propanone Cyanogen, EthanedinitrUe, Dicyan, Oxalic acid dinitrUe, Dicyanide Chloroacetone, l-Chloro-2-propanone... 

The unstable sodium salt of 5-chloro-3-mercapto-l,2,4-thiadiazole (336)151 reacts also with cyanogen bromide forming 5-chloro-3-thio-cyanato-l,2,4-thiadiazole (337).202 The sparingly soluble neutral sodium salt of 5-hydroxy-3-thiocyanato-l,2,4-thiadiazole (339) is similarly obtained (336->338->339) its free acid, like other 5-hydroxy-l,2,4-thiadiazoles, is fairly strong, but unstable.202... 

Mono- and di-thiocyanato-1,2,4-thiadiazoles, obtained by the stepwise action of cyanogen bromide on barium 3,5-dimercapto-l,2,4-thiadiazole, and on 5-chloro- and 5-hydroxy-3-mercapto-1,2,4-thiadiazole, are somewhat labile. The structures of certain of their transformation products (e.g. mono- and di-sulfides), which may have one of several isomeric forms, are not fully elucidated. The reactivity of their cyano group, resembling that in cyanogen halides, is noteworthy it is easily removed by the action of alkalis, the parent thiol being regenerated.202... 

Ammonium perchlorate, Impurities, 3998 Azidoacetic acid, 0770 f Aziridine, Acids, 0859 Benzoyl azide, 2694 Benzyl chloroformate, 2926 1,2-Bis(difluoroamino)-/V-nitroethylamine, 0799 Bromine trioxide, 0259 2-Butanone oxime, 1649 2-Butyne-l,4-diol, 1523 Butyraldehyde oxime, 1650 Carbon, Unsaturated oils, 0297 Chlorine, Carbon disulfide, 4041 f l-Chloro-2,3-epoxypropane, Contaminants, 1158 Cyanogen chloride, 0322 Diethyl phosphorochloridate, 1675 f 1,1-Difluoroethylene, 0696... 

Chloro-2-nitrobenzylchloride Cyanogen bromide Ethylglycine hydrochloride Ferric chloride anhydrous Chlorine Bromine... 

Chloro-l,2,3,5,-tetrahydroimidazo[2,l-b]quinazolin-2-one was produced from 6-chloro-2-nitrobenzylchloride, ethylglycine hydrochloride and cyanogen bromide in 3 steps. 

The pyrolysates obtained at 700-1100 K from 1,1,2-trichloronitroso-ethane 32 and having the ionic peaks at m/z 30 and m/z 62 were determined to be formaldehyde and cyanogen chloride by microwave spectroscopy the above fragments were supposed to be produced by cleavage of 4/7-1,2-oxazete 33, generated by intramolecular cyclization of 1-chloro-l-nitroso-ethene CH2 = C(Cl)-NO (Scheme 8) <2000MI177>. 

Baxter, G.P., Bezzenberger, F.K., Wilson, C.H. (1920) The vapor pressures of certain substances Chloropicrin, cyanogen bromide, methyl-dichloro-arsine, phenyl-dichloro-arsine, diphenyl-chloro-arsine and arsenic trichloride. J. Am. Chem. Soc. 42, 1386-1393. 

Chloral chloretoxyfos, chloralose, DDT, dichlorvos, dicofol, methoxychlor, naled, plifenate, trichlamide, trichlorfon, triforine Chlordane heptachlor Chlordene chlordane Chlorine cyanide see cyanogen chloride Chloro acetaldehyde nipyraclofen, oxabetrinil Chloro acetone pymetrozine Chloro acetonitrile thicyofen... 

A modification of the reaction of a-aminoacetonitrile (37a) has been developed which leads to 3,4-dichloro-l,2,6-thiafiiazole (39) in over 80% yield. The action of commercial sulfur dichloride on 37a produces a 1-1 mixture of 3-chloro- and 3,4-dichloro-l,2,5-thiadiazole, (38 and 39). However, if excess chlorine is added to the reaction mixture the dichloro compound forms exclusively in 82 % yield. It was shown that the dichloro compound does not form via chlorination of 3-chloro-1,2,5-thiadiazole. Therefore, either chlorination takes place on one of the intermediates prior to aromatization or the amino-acetonitrile is oxidized by the chlorine-sulfur dichloride mixture to cyanogen which is known to react with the sulfur chlorides to form 39 (see Section II,B,4). 

Cyanoformamide (40), formed in quantitative yield by the acid-catalyzed reaction of cyanogen with water, is converted into 3-chloro-4-hydroxy-l,2,5-thiadiazole (41) by reaction with sulfur monochloride.Prior conversion of 40 to the imino ether (42) leads to 3-ethoxy-4-hydroxy-l,2,5-thiadiazole (43). 

The reaction products of cyanogen with alcohols, dialkyl oximidates (44) and alkylcyanoformimidates (45), also available through the reaction of sodium cyanide with chlorine in aqueous alcohol, both react with the sulfur chlorides forming the appropriately substituted thiadiazole. Wen reported the synthesis of diethoxy-1,2,5-thia-diazole (46) from 44 and sulfur dichloride. Several analogs of 45 were converted to 3-chloro-4-alkoxy-l,2,5-thiadiazoles (46a) by treatment with sulfur monochloride. 

A strong base. Vigorous reaction with 1,2,4,5-tetrachlorobenzene has caused many industrial explosions and forms the extremely toxic 2,3,7,8-tetrachlorodibenzodioxin. Mixmres with aluminum + arsenic compounds form the poisonous gas arsine. Potentially explosive reaction with bromine, 4-chlorobutyronitrile, 4-chloro-2-methylphenol (in storage), nitrobenzene + heat, sodium tetrahydroborate, 2,2,2-trichloroethanol, zirconium + heat. Reacts to form explosive products with ammonia + silver nitrate (forms silver nitride), N,N -bis(trinitroethyl)urea (in storage), cyanogen... 

Treatment of diphenylacetonitrile in toluene with sodium amide and 2-chloro-pyrazine gave 2-(C-cyano-C,C-diphenylmethyl)pyrazine (1021), and 2-vinylpyrazine with phenylacetonitrile and sodium heated at 120-130° for 10 minutes gave 2-(3 -cyano-3 -phenylpropyl)pyrazine (731). 2-Amino-5-bromomethyl-3-cyano-pyrazine with sodium hydride and methyl cyanoacetate in tetrahydrofuran formed the dialkylated product (56) (1031). 2-Amino-3-mercapto-5,6-dimethylpyrazine in methanol with potassium hydroxide and chloroacetonitrile gave 2-amino-3-cyanomethyIthio-5,6-dimethylpyrazine (1229), and 2-carboxypyrazine refluxed with chloroacetonitrile and triethylamine in ethyl acetate for 45 minutes gave the cyanomethyl ester (1317). 2-Hydroxy 5-methyl-3-propylpyrazine with cyanogen halides in aqueous sodium hydroxide-dimethylformamide at 0-5° gave l-cyano-5-methyl-2-oxo-3-propyl-l, 2-dihydropyrazine (1123). 

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