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Thiadiazoles and Thiadiazolines. Part 1. Reaction of Thiourea and Ethylenethiourea with Chlorodiazabutadienes: a New Route to 4-Amidino-1,3,4-thiadiazolines

DOI: 10.1039/P19810000360

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 360 - 365 (1981)

Update date:2022-07-30

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Authors:

Askari, Syed H.Askari, Syed H.

Moss, Stephen F.Moss, Stephen F.

Taylor, David R.Taylor, David R.

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Article abstract of DOI:10.1039/P19810000360

1-Chloro-1,4-diaryldiazabutadienes (1) react with thiourea to give hydrochlorides of 4-amidino-2,5-diaryl-Δ2-1,3,4-thiadiazolines from which the corresponding free bases (2) are obtained by treatment with cold alkali.Imidazolidine-2-thione (ethylenethiourea) reacts similarly with the chlorodiazabutadienes (1a,b) to give, after treatment with cold alkali, 4-(4,5-dihydroimidazolin-2-yl)-2,5-diaryl-Δ2-1,3,4-thiadiazolines (6a,b).In the presence of an excess of sodium borohydride the reaction of (1a) with thiourea yielded some N2-benzylthiobenzoylhydrazine (12), compatible with the capture of an intermediate iminium ion.A mechanism is suggested for these reactions.

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Product name:4-(4,5-dihydroimidazolin-2-yl)-2-(4-chlorophenyl)-5-phenyl-Δ2-1,3,4-thiadiazoline hydrochloride

Cas No:77436-18-1

77436-18-1

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