Disulfide hydrazine

Hydrazine as Nucleophile. Reaction of hydrazine and carbon dioxide or carbon disulfide gives, respectively, hydrazinecarboxyhc acid [471-31-8], NH2NHCOOH, and hydrazinecarbodithioic acid [471-32-9], NH2NHCSSH, in the form of the hydrazinium salts. These compounds are useful starting materials for further synthesis. For example, if carbon disulfide reacts with hydrazine in basic medium with an alkyl haUde, an alkyl dithiocarbazate ester is obtained in a one-step reaction ... 

Isothiazolium salts (59) react with phenylhydrazine to give pyrazoles (60) (72AHC(14)l) (see Section 4.02.1.6). When treated with hydrazine hydrate, 3-chloro-l,2-benzisothiazole gives di-(o-cyanophenyl) disulfide (73SST(2)556), but 2,1-benzisothiazole gives o-aminobenz-aldehyde azine (72AHC( 14)43). 2-Substituted saccharins give the expected o-sulfamoyl-benzohydrazides. 

The monothioacetal is also stable to 12 N hydrochloric acid in acetone (used to remove an TV-triphenylmethyl group) and to hydrazine hydrate in refluxing ethanol (used to cleave an A -phthaloyl group). It is cleaved by boron trifluoride etherate in acetic acid, silver nitrate in ethanol, and tiifluoroacetic acid. The monothioacetal is oxidized to a disulfide by thiocyanogen, (SCN)2- ... 

Chloroformates or carbonyl chloride react with 2-piperidone hydrazones to give triazolopyridine-3-ones (86JAP(K)69776), and there are further examples of the production of 3-thiols from a hydrazine and carbon disulfide (83USP4419516, 88EUP254623). 

The reaction of l-acetyl-3-indolinone 124 with carbon disulfide in the presence of sodium hydride gave thiazolo[3,4-with hydrazine or phenylhydrazine gave 2H[ 1,2,4]triazino[4,5-a]in-dole 126 (75YZ980) (Scheme 29). 

Hydrazinotriazine 749 was prepared by the condensation of the respective quinone with thiosemicarbazide followed by sequential cyclization, chlorination with phosphorus oxychloride, and reaction with hydrazine (88JHC1139). Cyclocondensation of 749 with formic acid or carbon disulfide gave triazolotriazines 750 (88JHC1139) (Scheme 156). 

Hydrazine 835 underwent ring closure with one carbon cyclizing reagents to afford 837 and/or /V-acyl derivatives 836. The N-acyl derivatives underwent cyclization on treatment with phosphorus oxychloride. They were also prepared by the reaction of hydrazones 838 with thionyl chloride (84JHC1565). Compound 835 underwent ring closure with carbon disulfide and ethyl chloroformate to give 839 (Scheme 169). 

N204 also forms expl mixts with incompletely halogenated hydrocarbons, NGu, carbon disulfide, etc (Ref 33). The effect of spontaneous decompn by oxidation-reduction reactions when N204 is mixed with a number of fuels (hydrazine, gasoline, liq paraffin, etc) has resulted in its extensive use in liq propint rocket engines (Refs 12, 22, 27 35)... 

Rzdtc) ] reacts with diethyl azodicarboxylate, azobenzene, or dimethyl acetylenedicarboxylate to give the appropriate hydrazine and disulfide... 

Disulfides can be reduced to thiols by mild reducing agents, such as zinc and dilute acid or Ph3P and H2O. The reaction can also be aceomplished simply by heating with alkali. Among other reagents used have been LiAlR, Mg/ MeOH, KBH(0—i-Pr)3, and hydrazine or substituted hydrazines. ... 

Similarly, condensation of 206 with carbon disulfide under basic conditions gives rise to the mercapto-substituted tricyclic system 207 in good yield (Equation 55) <2000AF904>. This approach has also been used for related systems of substituted pyrimidines <1999JHC1119, 2000PS( 163) 1 >. Hydrazine-substituted pyrimidines have also been reacted in an analogous manner <1998JRM1248>. 

Thiadiazinotriazolopyrimidines can be prepared in several ways from the hydrazine-substituted thiadiazino-pyrimidine 186. Reaction with carbon disulfide gives the thione 187 reaction with either anhydrides or orthoformates with sulfuric acid gives the substituted triazoles 188, and reaction with cyanogen iodide gives the aminotriazole 189 (Scheme 47) <2004HC0335>. 

Thiation of [l,2,4]triazino[3,2-h]quinazoline-3,10-dione 782 with phosphorus pentasulfide in pyridine proceeded selectively to give the 3-thioxo analogue 783. The latter was converted to the corresponding 3-methylthio derivative 784 by reaction with methyl iodide. Treatment of 784 with hydrazine gave 785, which was converted to 786 and 787 by cyclization with formic acid or carbon disulfide (90JHC591). Cyclization of 785 with sodium nitrite in hydrochloric acid gave 788 (90JHC591). 

Nitric oxide and gases Aluminum, BaO, boron, carbon disulfide, chromium, many chlorinated hydrocarbons, fluorine, hydrocarbons, ozone, phosphine, phosphorus, hydrazine, acetic anhydride, ammonia, chloroform, Fe, K, Mg, Mn, Na, sulfur... 

The reaction of compound 376 with hydrazine gives product 377 that has been transformed into similar triazoles 378, after reaction with carbon disulfide in the presence of alcoholic potassium hydroxide, benzoic acid in the presence of phosphoms oxychloride, or 3-[bis-(methylthiomethylene)]pentan-2,4-dione and l,l-dicyano-2,2-dimethylthioethylene, in refluxing -butanol (Scheme 40) (Table 55) <2000FES641>. 

Hydrazines of type 89 react with various carbonic acid derivatives to furnish cyclized product. Under basic conditions (KOH), in the presence of carbon disulfide or arylisothiocyanates, the cyclized thione 90 is obtained (Scheme 7) <1966JOG3528, 1984JCCS315>. Analogous reactions performed in the absence of base gave 91 as a 3-thiol when performed with carbon disulfide, as a 3-hydroxyl with methyl chloroformate, or as a 3-arylamino with arylisothiocyanates in the presence of dicyclohexylcarbodiimide (Scheme 7) <1986JHC1339, 1992IJB467>. 

See also thermite reactions Carbon disulfide Air, Rust Hydrogen sulfide Rust Hydrazine Rust... 

Types of compounds are arranged according to the following system hydrocarbons and basic heterocycles hydroxy compounds and their ethers mercapto compounds, sulfides, disulfides, sulfoxides and sulfones, sulfenic, sulfinic and sulfonic acids and their derivatives amines, hydroxylamines, hydrazines, hydrazo and azo compounds carbonyl compounds and their functional derivatives carboxylic acids and their functional derivatives and organometallics. In each chapter, halogen, nitroso, nitro, diazo and azido compounds follow the parent compounds as their substitution derivatives. More detail is indicated in the table of contents. In polyfunctional derivatives reduction of a particular function is mentioned in the place of the highest functionality. Reduction of acrylic acid, for example, is described in the chapter on acids rather than functionalized ethylene, and reduction of ethyl acetoacetate is discussed in the chapter on esters rather than in the chapter on ketones. 

Hydrazine reacts with carbon disulfide to yield dithiocarbazic acid [471-32-9] N2H4 + CS2 NH2NHCSSH... 

Alkylthio com ounds 16 (R = Ph) are oxidized by 30% hydrogen peroxide,or by potassium permanganate to the corresponding A -imidaz-olin-5-one sulfuryl chloride transforms disulfide 19 into 24. Alkylthio groups are not displaced by hydrazine ... 

Dimethylhydrazine, N,N Unsymmetrical Dimethylhydrazine under Hydrazine Derivatives Dimethyl Sulfide under Sulfides, Disulfides Dinitrotoluene under Simple Aromatic Nitro Compounds... 

Nucleophilic substitution of the 4-chloro group of the 4-pyranotriazines 103 with hydrazine gives the 4-hydrazino-triazines 104, which can be further elaborated to the corresponding azides 105 or cyclized upon reaction with formic acid or carbon disulfide to give the triazolotriazines 106 or thioxotriazolotriazines 107, respectively (Scheme 11) <2005HC0495>. 

Compound 279, prepared from the corresponding chloro derivative, is converted into 280 upon treatment with ethyl orthoformate under mild conditions. Heating 2TO in neutral solvents gives 281 (81JCS(PI)2387). The hydrazine 279 (R = Me) is converted into 282 on treatment with carbon disulfide in DMF (77GEP2838029). The hydrazone 283 is formed from 284 and 5-nitrofuranal (76JMC512). 

Chemicals which can damage (a) the liver include carbon tetrachloride, paracetamol, bromobenzene, isoniazid, vinyl chloride, ethionine, galactosamine, halothane, dimethyl-nitrosamine (b) the kidney include hexachlorobutadiene, cadmium and mercuric salts, chloroform, ethylene glycol, aminoglycosides, phenacetin (c) the lung include paraquat, ipomeanol, asbestos, monocrotaline, sulfur dioxide, ozone, naphthalene (d) the nervous system include MPTP, hexane, organophosphoms compounds, 6-hydroxydopamine, isoniazid (e) the testes include cadmium, cyclophosphamide, phthalates, ethanemethane sulfonate, 1,3-dinitrobenzene (f) the heart include allylamine, adriamycin, cobalt, hydralazine, carbon disulfide (g) the blood include nitrobenzene, aniline, phenyl-hydrazine, dapsone. 

Hydrazine Azide (formerly called Hydrazine Azoimide,Hydrazine Trinitride or Hydrazonium Azide) (called by Curtius Diammonium Azide, N,H ), NaH, HN, mw 75.08, N93.29% rhmb, hygr crysts mp 75.4(Ref 6) v sol in w, sol in hydrazine(190% at 23 ), methanol (6.1% at 23°) and in ale (1.2% at 23°C), not appreciably sol in chlf, carbon tetrachloride benz, carbon disulfide, ethyl acetate or diethyl ether (Ref 6). First prepd by Curtius in I89I (Ref 1) by neutralizing hydrazoic acid with hydrazine... 

Synthesis from hydrazine, hydroxylamine and hydrogen disulfide 556... 

A number of mesoionic l,2,4-triazolo[4,3-a]pyrimidines (15) were obtained upon desulfurization of l-methyl-l-(4,6-dimethylpyrimidin-2-yl)thiosemicarbazides (13) with dicyclohexylcarbodiimide (DCC) [88JCS(CC)506 93JCS(P1)705] or by cyclization of l-alkyl-l-(4,6-dimethylpyrimidin-2-yl)hydrazines (14) with carbon disulfide or phosgene [88JCS(P1)351] (Scheme 8). 

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