Dithiocarboxylic acid esters chlorides

Sodium hydrogen sulfide Thiocarboxylic acid chlorides from dithiocarboxylic acid esters via dithiocarboxylic acids... 

Dithiocarboxylic acid esters. 1.5-2 moles of phosgene passed at 25-30° into a soln. of propionic acid piperidide in toluene, and the product isolated after 4-5 hrs. propionic acid piperidide chloride (Y 90-95%) suspended in abs. ether, treated at 0° with ethyl mercaptan, the ether removed, the residue treated with dimethylformamide and pyridine, HgS introduced 4 hrs. at 0°, and allowed to stand several hrs. at room temp. ethyl dithiopropionate (Y 86%). F. e., also thionocarboxylic acid esters by initial treatment with alcohol, isolation of thiolic acid esters, and f. reactions, also ring closures to hetero-cyclics, s. H. Eilingsfeld, M. Seefelder, and H. Weidinger, B. 96, 2671 (1963). 

Prepn. from N,N-disubst. carboxylic acid amides—Thiocarboxylic acid esters Dithiocarboxylic, thiolic, and thionocarboxylic acid esters—Ring closures to heterocyclics s. 19, 628 a-chlorimmonium chlorides cf. M. Grdini6 and V. Hahn, J. Org. Chem. 30, 2381 (1965)... 

The thioacylation of NH groups by dithiocarboxylic esters and their salts, as well as by thionocarboxylic esters, is dealt with in Section 5 of this chapter. Diphenylcyclopropenethione reacts with amines to give the cycloadducts (91), which are rearranged to the thioamides (92) when heated in benzene. Thioamides RNHC(S)CHXY are obtained from compounds with active methylene groups by reaction with A-aryldithiocarbamic acid esters, e.g. MeSC(S)NHPh, thiocarbamoyl chlorides, or C-sulphonylthioformamides,... 

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