Synthesis of Nitro‐ and Amino‐Substituted Thiobenzamides by Thiolation Reactions with Elemental Sulfur at Mild Conditions
The Synthesis of thiobenzamides 2–7 by basecatalyzed thiolation of nitro‐benzyl‐halides (type 1), especially at low temperatures, and the selective synthesis of p‐ and m‐nitro‐thio‐benzamides (2, 3) or p‐and m‐amino‐thiobenzamides (5, 6), respectively, are described. o‐Nitro‐benzylhalides (→ 4, 7) are less reactive than p‐ and m‐nitro‐benzylhalides.
The reaction of nitrobenzylhalides (type 1) with elemental sulfur and amines occuring at low temperatures to give 2–4 leads via structures of the type 11, 15 and 16.