Chlorophenyl Isothiocyanate

Chlorophenyl isothiocyanate has also been prepared by treating an alcoholic solution of sym-di-/)-chlorophenyl thiourea with iodine/ from ammonium -chloroplienyldithiocarbamate and lead nitrate/ (p. 72), and from the action of thiophosgene with /)-chloroaniline. ... 

Chlorophenyl isothiocyanate [2131-55-7] M 169.6, m 44 , 43-45 , 45 , 46 , 47 , b 110-115 /4mm, 135-136 /24mm. Check the IR first. Triturate with pet ether (b 30-60°) and decant the solvent. Repeat 5 times. The combined extracts are evap under reduced press to give almost pure compound as a readily crystallisable oil with a pleasant anise odour. It can be recrystd from the minimum vol of EtOH at 50° (do not boil too long in case it reacts). It can be purified by vac distn. IRRITANT. [Org Synth Coll Vol V 223 7 975.1... 

Diethyl malonate was reacted with 4-chlorophenyl isothiocyanate in the presence of sodium hydride in dioxane at room temperature for 1 hr to give the sodium salt of mercapto-(4-chlorophenylamino)methylenemalonate, which was then treated with ethylene dibromide in DMF at room temperature overnight. In this way, diethyl [3-(4-chlorophenyl)-l,3-thiazolidin-2-ylidene]malonate was obtained in 88% yield (82EUP58392). 

The creamy suspension is allowed to cool to room temperature, and the electrodes of a pH meter are inserted (Note 4). A solution of 20.5 g. (0.15 mole) of zinc chloride (Note 5) in 75 ml. of water is added dropwise with vigorous stirring over a period of 45 minutes, while the pH is maintained at 7 by the simultaneous dropwise addition of a 4A aqueous solution of sodium hydroxide (Note 6). The mixture is stirred for 1 hour and is then filtered with suction the solid product is dried under reduced pressure over phosphorus pentoxide. The dry material is slurried with 200 ml. of petroleum ether (b.p. 30-60°), and the solvent is decanted. This process is repeated five times, and the combined extract is evaporated at reduced pressure. The yield of almost pure -chlorophenyl isothiocyanate, obtained as a readily crystallizing oil with a pleasant anise-like odor, is 33-35 g. (65-68%), m.p. 44-45°. The product can be recrystallized from the minimum amount of ethanol at 50°. 

CHLOROPHENYL ISOTHIOCYANATE (Isofhiocyanic acid, >-chlorophenyl ester)... 

Caution p-Chlorophenyl isothiocyanate may cause severe dermor-iitis if allowed to come in contact with the skin. This preparation should he carried out in a good hood, and rubber gloves should be worn throughout. 

The procedure given here is essentially that described previously by the submitters. -Chlorophenyl isothiocyanate has been prepared from sym-di-p-chloiophenyl thiourea with iodine in alcoholic solution, from ammonium p-chlorophenyldithio-carbamate and lead nitrate [cf. also Org. Syntheses, Coll. Vol. 1 447 (1932)], by the action of thiophosgene on />-chloroaniline and from -chloroaniline with thiocarbonyl tetrachloride in the presence of stannous chloride. ... 

C6H1403 dipropylene glycol 25265-71-8 -40.15 1.2586 2 9478 C7H3BrCINS 4-bromo-2-chlorophenyl isothiocyanate 98041-69-1 25.00 1.7934 2... 

Chlorobenzyl isothiocyanate [3694-45-9] 4-Chlorophenyl isothiocyanate [2131-55-7] 4-Cyanophenyl isothiocyanate [2719-32-6] Cyclohexyl isothiocyanate [1122-82-3] Ethylene diisothiocyanate [3688-08-2]... 

A refluxing soln. of p-chlorophenyl isothiocyanate in dimethyl sulfoxide treated with water during 10 min. 1,3-di-p-chlorophenylthiourea. Y 87%. F. e., also in dimethylformamide, s. D. Martin and W. Mucke, Monatsber. Deut. Akad. Wiss. Berlin 6, 362 (1964) C. A. 62, 3960a. 

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