Synthesis and characterization of N-thiophosphorylated thioureas RC(S)NHP(S)(OiPr)2 (p-(4-imidazol-1-yl)-C6H4NH, p-NC-C6H4NH, (CH2CH-CH2)2N): Unexpected formation of o-HO-C6H4NHC(S)NHP(S)(OiPr)2 from p-NC-C6H4NHC(S)NHP(S)(OiPr)2

Reaction of p-(4-imidazol-1-yl)-C6H4NH2, p-NC-C6H4NH2 or (CH2CH-CH2)2NH with O,O′-diisopropylthiophosphoric acid isothiocyanate (iPrO)2P(S)NCS leads to p-(4-imidazol-1-yl)-C6H4NHC(S)NHP(S)(OiPr)2 (HLI), p-NC-C6H4NHC(S)NHP(S)(OiPr)2 (HLII) and (CH2CH-CH2)2NC(S)NHP(S)(OiPr)2 (HLIII). Recrystallization of HLII from 96% aqueous EtOH solution leads to the formation of o-HO-C6H4NHC(S)NHP(S)(OiPr)2 (HLIV).