Publication details
Syntheses and reactivity of alkyl 1-[N-(2-chloro-5-nitro-phenyl)-benzimidoyl] thioureas
| Authors | |
|---|---|
| Year of publication | 2012 |
| Type | Article in Periodical |
| Magazine / Source | Journal ofSulfur Chemistry |
| MU Faculty or unit | |
| Citation | |
| Doi | http://dx.doi.org/10.1080/17415993.2011.629094 |
| Field | Organic chemistry |
| Keywords | thiourea–isothiourea rearrangement; SNAr reaction; benzimidoyl thiourea; benzothiazole |
| Description | A series of new alkyl 1-[N-(2-chloro-5-nitro-phenyl)-benzimidoyl] thioureas 3a–h were prepared from benzamides 1a–c. Benzimidoyl thioureas 3a–e afforded 5-nitro-2-phenyl-benzothiazole 5a–c under basic conditions via thiourea–isothiourea rearrangement and SNAr. A mechanistic rationalization supported by the direct formation of benzothioamide 8 and bis-benzimidoyl sulfide 9 derivatives from the reaction of imidoyl isothiocyanate 2 with bulky amines was supported. |