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From o-Aminobenzenethiols

From o-Aminobenzenethiols (Type A S—C H4—N + C).—An improvement on the standard procedures (milder conditions) is the use of DMF dimethyl acetal instead of formic acid or alkyl orthoformates. A 64% yield of benzothiazolin-2-one is obtained when o-aminobenzenethiol is treated sequentially with carbon monoxide and oxygen in the presence of triethylamine and selenium in DMF. o-Aminobenzenethiol forms substituted vinylamine adducts with acetylenic nitriles RC=CCN. These cyclize in the presence of sodium ethoxide, and the products lose acetonitrile on distillation at atmospheric pressure to give 2-sub- [Pg.386]

Sonoda, G. Yamamoto, K. Natsukawa, K. Kondo, and S. Murai, Tetrahedron Letters, 1975. 1969. [Pg.386]

Diethyl monothiono-oxalate, EtOC(S)COaEt, reacts with o-aminobenzenethiol to give ethyl benzothiazole-2-carboxylate (1 R = COaEt), while esters of [Pg.387]

An intermediate has been isolated from the reaction between o-aminobenzene-thiol and dimethyl cyanimidodithioate (see Vol. 3, pp. 617, 618) this yields bis(benzothiazol-2-yI)amine, thus further elucidating the mechanism.  [Pg.387]


Stephens WD, Field L (1959) A seven-membered heterocycle from o-aminobenzenethiol and chalcone. J Org Chem 24 1576... [Pg.88]


See other pages where From o-Aminobenzenethiols is mentioned: [Pg.538]   


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