4-Nitrophenyl isothiocyanate

Piperazine NH group of 9-fluoro-10-(l-piperazinyl)-7-oxo-2,3-dihydro-7//-pyrido[l,2,3-<7e]-l,4-benzothiazine-6-carboxylate was reacted with 4-nitrophenylsulfonyl chloride, 2,6-dichloropyrazine, 2,6-dichloropyridine in DMF in the presence of pyridine, and with 4-nitrophenyl isothiocyanate in aqueous acetone in the presence of KOH (01MIP13). A side chain amino group on a 2,3-dihydro-7//-pyrido[l,2,3- fe]-l,4-benzothiazin-7-one skeleton was acylated (OOMIPIO). 

The second step involved the conversation of 2,6-dichloro-4-nitrophenyl-isothiocyanate to 1-(2-aminoethyl)-3-(2,6-dichloro-4-nitrophenyl)-thiourea ethylenediamine solvate. The solution of 2,6-dicloro-4-nitrophenyl-isothiocyanate (432 g, 1.73 mol) in 2 L of toluene was added dropwise to the cooled (0°C) solution ethylenediamine (244 ml, 3.66 mol, 2.1 eq.) in toluene (4 L) under a nitrogen atmosphere. 2-Propanol (1 L) was added and after 5 minutes, the solid was collected by filtration, washed with 20% 2-propanol/toluene, and dried to a constant weight of 602 g (94%). This product is hygroscopic, mp 120°C (dec.). 

Colored reagents to follow the appearance or the disappearance of a functional group have been widely used to monitor reactions in classical organic chemistry, particularly in TLC analysis. This technique has been successfully adapted to SPS for example, ninhydrin (118), bromophenol blue (119), nitrophenyl isothiocyanate-O-trityl (120), picric acid (121), and malachite green isothiocyanate (122) have all been used to show the presence or the absence of free resin-bound amines. The presence of free resin-bound thiol groups can also be detected (123). 

Heating of the cycloadduct derived from 4-nitrophenyl isothiocyanate and dicyclohexyl-carbodiimide causes cycloreversion to give the starting materials In the reaction of phenylcarbonyl isothiocyanate and substituted phenylcarbonyl isothiocyanates, respectively, with carbodiimides, [2-1-4] cycloadducts 221 are usually obtained, but the [2 + 2] cycloadduct 220 is also formed when the reaction of DCC with phenylth-iocarbonyl isothiocyanate is stopped at shorter reaction times. ... 

Trapping of 1,3-diazahepta-l,2-diene with 4-nitrophenyl isothiocyanate affords the [2-1-2]... 

Satchell and Satchell" reported a kinetic study on the aminolysis of p-nitrophenyl isothiocyanate with primary amines and anilines in diethyl ether and isooctane as solvents. The detailed analysis reveals that the aminolysis occurs via a zwitterionic intermediate, T , which undergoes subsequent proton transfer catalyzed by a second amine molecule (equation 12). Added carboxylic acids form inactive 1 2 amine-acid complexes with strong basic amines and inhibit aminolysis, but with weak bases the acids form only a negligible amount of complex and they catalyze the aminolysis. 

The chlorination of isothiocyanates and dithiocarbamates is a general method and good yields of carbonimidoyl dichlorides are obtained. However, on attempted conversion of o-nitrophenyl isothiocyanate a reaction mixture was obtained, which decomposed violently upon heating... 

A soln. of l-cyclohexyl-2-phenyl-3-p-toluoylaziridine and p-nitrophenyl isothiocyanate refluxed 17 hrs. in dry benzene -> 3-cyclohexyl-5-p-nitrophenylamino-2-phenyl-4-p-toluoyl 4-thiazoline. Y 54%. J. W. Lown,G. Dallas, and T. W. Maloney, Can. J. Chem. 47, 3557 (1969) aziridine ring expansion, review, s. F. N. Gladysheva, A. P. Sineokov, and V. S. Etlis, Russ. Chem. Rev. 39, 118 (1970) (Eng. transL) heterocyclics by aziridine ring expansion, review, s. J. W. Lown, Record Chem. Progr. 32, 51 (1971). 

The enantioselective [2-1-2] cycloaddition of ketenes to 4-nitrophenyl isothiocyanate using an NHC catalyst was demonstrated. It is interesting to note that [2-1-2-1-2] cycloadduct 178 was obtained when benzoyl isothiocyanate was used instead. The benzoyl group may stabilise the NHC-ketene-isothiocyanate intermediate and facilitate its addition to a second molecule of the ketene, thus leading to the [2 -f 2 -F 2] cycloaddition reaction (Scheme 20.74). 

In the reaction of p-nitrophenyl isothiocyanate with AT,W-tetramehtyl-W"-n-butyl-guanidine 49 an exchange reaction with formation of n-butyl isothiocyanate 50 is observed. ... 

A 1,3-dipole, generated from the aziridine 91, also undergoes a [3-1-2] cycloaddition reaction with p-nitrophenyl isothiocyanate to give a thiazolidine derivative 92 . ... 

Similar [3+2] cycloaddition products are obtained in the reaction of 104 with 4-nitrophenyl isothiocyanate and phenylcarbonyl isothiocyanate. 

Phenyl isothiocyanate 4-Nitrophenyl isothiocyanate Trifluoromethyl phenyl isothiocyanate 4-Cyanophenyl isothiocyanate 4-Methoxyphenyl isothiocyanate 4-Fluorophenyl isothiocyanate 4-Methylphenyl isothiocyanate 2-Fluoro-5-(trifluoromethyl)phenyl isothiocyanate 4-Methyl-3-(trifluoromethyl)phenyl isothiocyanate 4-Fluoro-3-(trifluoromethyl)phenyl isothiocyanate 3,5-Bis(trifluoromethyl)phenyl isothiocyanate 1,4-Phenylene diisothiocyanate... 

Here, the isothiocyanate containing aromatic compoimd receives electron on the negative electrode surface and is reduced to a radical. The thus produced radical acts as a polymerization initiator in the polymerization reaction. In addition, since the radical is continuously easily produced with the pol5meiization reaction, the polymerization reaction may be continuously occurring. In this way, a solid electrolyte interface film may be produced on the negative electrode surface. It has been found that the reduction potential of 4-nitrophenyl isothiocyanate was remarkably lower than the reduction potential of ethylene carbonate (93). 

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