Herz Reaction

R. Herz, DE 360690 (1914 to Cassella & Co.); US 1637023 (1928); US 1699432 (1929).

Formation of o-aminothiophenols by heating aromatic amines with excess monochloride. The initial products are thiazothionium halides (Herz compounds) which will undergo chlorination if the position para to the amino group is unsubstituted:



W. K. Warburton, Chem. Rev. 57, 1011 (1957); L. D. Huestis et al., J. Org. Chem. 30, 2763 (1965); P. Hope, L. A. Wiles, J. Chem. Soc. C 1967, 1642; B. K. Strelets, L. S. Efros, Zh. Org. Khim. 1969, 153; S. W. Schneller, Int. J. Sulfur Chem. 8, 579 (1976); B. L. Chenard, J. Org. Chem. 49, 1224 (1984).