Preparation, Thermolysis, and Photolysis of Some New Thiophosphoramidates Derived from 3-Methyl-2-Benzothiazolinone Hydrazone

Abstract

3-Methyl-2-benzothiazolinone hydrazone (1) reacts with dialkyl phosphorothiochloridates 2a,b in the presence of a base, to give the respective dialkylthiophosphorylated hydrazones 3a,b. Upon thermolysis, compound 3b yields bi(3-methylbenzothiazole-2-iminyl) (4). Exposure of 3b to sunlight in methanol results in the formation of 3-methyl-2-benzothiazolinone (5). When the same experiment was carried on the starting hydrazone 1, bis(3-methyl- benzothiazole-2-iminyl)diazine (6) was formed. Elemental analyses and spectroscopic details are presented for the new compounds.

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Keywords:

• 3-Methyl-2-benzothiazolinone hydrazone
• photolysis
• thermolysis
• thiophosphorylation
• X-ray crystallography

Notes

*Temperature: 298 K, wavelength: MoK_α (0.71073 Å).

**Two independent molecules are present in the same asymmetric unit cell, therefore the value is doubled.