Chloroethyl isothiocyanate

A similar type of reaction is observed with the intermediate (381) resulting from the reaction of a secondary amine, a thiol or an alcohol, with /3 -chloroethyl isothiocyanate (380 Scheme 234) (75SC143). 

The reaction of 2-chloroethyl isothiocyanate with ethylene sulfide in the presence of Et4N+Br (20 d, 20 °C) gave an 83% yield of 2,3,5,6-tetrahydrothiazolo[2,3-h]thiazolium chloride (265) by way of intermediate (264) (71CHE1534). The identical ring system is formed on treatment of V,lV-bis(2-chloroethyl)amine and CS2 in aqueous NaOH (63JPR(291)10l). With 2-chloroethyl isothiocyanate and N-phenylethyleneimine, in the absence of a catalyst, imidazo[2,1 -hJthiazolium chloride (266) is obtained in 60% yield. 

An interesting cyclization reaction on AlCA-riboside with 2-chloroethyl isothiocyanate to give a dihydrothiazolo[3,2-a]purine riboside 19 has recently been reported. 

Chloroethyl isothiocyanate 811 2-Chloroethylammonium chloride (50 g), dissolved in water (100 ml), and chloroform (200 ml) are stirred together and cooled in ice while a concentrated aqueous solution of calcined sodium carbonate (130 g) and a solution of thio-phosgene (50 g) in chloroform (50 ml) are dropped in simultaneously the solution must remain alkaline throughout this addition. After a further 0.5 hour s stirring, the chloroform layer is separated, dried over sodium sulfate, and fractionated. The product boils at 80°/13 mm. 

The interaction of 2-chloroethyl isothiocyanate and N-phenylethyl-enimine in triethylamine yields the substituted 2-iminothiazolidine (210). In the absence of the tertiary base, the reduced imidazo[2,l-b]thiazole (211) is formed as a by-product, possibly by the mechanism shown. ... 

Cyclization of the isothiocyanates obtained from alicyclic )8-amino esters with thiophosgene and 2-chloroethyl or 3-chloropropylamine gave the thia-zolopyrimidinones 464-467 (96UP2). 

The reaction of isothiocyanate 2 and 30 with 2-amino-4-picoline has also been reported.55 Dorn and coworkers56"59 reported the synthesis of a number of substituted thioureido derivatives by treatment of isothiocyanates 2 and 5 with 2-phenylethylamine, bis(2-chloroethyl)amine, and 2-(4-ethoxyphenyl)-1 -phenylethylamine. 

Ethyl carbamate Allyl isothiocyanate Methyl oxalate Ethyl bromoacetate Bis(2-chloroethyl) ether Glycol monoacetate 1-Iodobutane Diethylene glycol Furfuryl alcohol Levulinic acid Propyl chloroacetate... 

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