N-Phenylthiourea

The ligands N-[bis(isopropoxy)thiophosphoryI]thiobenzamide and N-[bis(isopro-poxy)thiophosphoryl]-N -phenylthiourea can be deprotonated with the acetylacetonate gold(III) derivative [Au(C6F5)2(acac)] [26] giving the corresponding pentafluorophenyl complexes with the ligand acting as a chelate one [192]. 

A series of 1-aminoalkanediphosphonic acids has been reported by the treatment of the N-phenylthiourea derivatives of a>-diethoxyphos-phinoylaldehydes with triphenyl phosphite.343 This constitutes an approach toward the analogues of aspartic and glutamic acid in which both carboxylate sites have been replaced by phosphonic acid functions. A similar approach has also been reported to be of use for the preparation of (diphenyl ester) phosphonate analogues of ornithine, lysine, and homolysine.344345... 

To a solution of triphenyl phosphite (6.2 g, 0.02 mol) and thiomethoxy-acetaldehyde (2.25 g, 0.025 mol) in glacial acetic acid (18 ml), powdered N-phenylthiourea was added in a single portion. The reaction mixture was stirred at room temperature for 30 min and then for 30 min at 80°C. After the mixture was cooled to room temperature, water (5 ml) was added and the solution was maintained at room temperature for 10 h. The precipitate was removed by suction filtration, washed with 1 1 acetic acidtwater (2 x 10 ml), dried over potassium hydroxide in an evacuated dessicator, and recrystallized from chloroform/ methanol. In this manner there was isolated pure 0,0-diphe-nyl 2-methylthio-l-(iV-phenylthioureido)ethylphosphonate (8.61 g, 94%) of mp 136 to 138°C, which exhibited spectra and analytical data in accord with the proposed structure. 

Pedersen (1971) reported on a number of crystalline complexes with thiourea and similar molecules and found that the solubility of dibenzo-18-crown-6 [11] in methanol is enhanced by urea and thiourea. The latter observation precludes the possibility of the solid complexes being urea or thiourea inclusion compounds. Factors that are of importance in the complex formation are ring size (dibenzo-12-crown-4 did not form complexes), and steric hindrance in the complex caused by the guest molecule. Thiourea, N-phenylthiourea, and 2-thiazolidinethione form complexes but N,N,N -trimethylurea, thiocarbanilide and N-methylthiazolidinethione do not. 

Fairwell, T., S. Ellis, and R.E. Lovins, Quantitative protein sequencing using mass spectrometry thermally induced formation of thiohydantoin amino acid derivatives from N-methyl- and N-phenylthiourea amino acids and peptides in the mass spectrometer. Anal Biochem, 1973. 53(1) 115-23. 

N 19.28% obtd with other products by uniting of Picryl chloride N-phenylthiourea in cold acetone or better in glac acet ac. It was isolated as the Pi crate, mp 82°, explodes at higher temp (Refs 1 2)... 

Zinc and hydrochloric acid remove the ring sulfur from 5-amino-1,2,4-thiadiazoles as hydrogen sulfide.6,85 5-Anilino-3-phenyl-l,2,4-thiadiazole (189) is slowly degraded, by the same reagent, to N-benzyl-N -phenylthiourea (191),129 probably by the usual ringopening at the N—S bond, followed by the further reductive hydrolysis of the intermediate (190) the latter can indeed be similarly reduced.129... 

SYNS NCI-C02017 PHENYLTHIOCARBAMIDE N-PHENYLTHIOUREA o-PHENYLTHIOUREA 1-PHENYLTHIOUREA PTC PTU RCRA WASTE NUMBER P093 U 6324 USAF EK-1569... 

The 6-keto-cholestane (354) was also converted by a known pathway into the lactam (355). Oxidation to the ketone (356a), followed by treatment with phenyl-hydrazine. gave the indole derivative (357). Brominatioh of the 3-ketone (356a) with pyridinum hydrobromide perbromide afforded the 4-bromo-ketone (356b). which in turn was allowed to react with N-phenylthiourea to furnish the thiazol (358) (Scheme 17). ... 

Metal compounds have found some application as desulfurization catalysts, and a novel reaction of N-phenylthiourea has been reported. The reaction of PhNCSNH2 with ethanolic Cu(OAc)2 in the presence of 2,2 -bipyridine results in the formation of the phenylcarbodiimido complex [(bipy)Cu(/i-PhN=C=N)2Cu(bipy)]. The same group have also described a related partial desulfurization of 3-methylimidazoline-2(l if)-thione to yield di( 1-methyl-imidazolyl)sulfide (41) upon reaction with copper(II) salts. These reactions are mechanistically obscure. 

FF is unstable in conditions of both light and heat. It will polymerize spontaneously at 230 C and some polymerization is likely to take place at temperatures as low as 60 °C. A stabilizer mixture consisting of N-phenylsubguanidine, N-phenylthiourea and N-phenylnaphthylamine at levels of 0.001-0.1% will prevent polymerization up to 170 °C. It follows, therefore, that care needs to be taken in distilling FF away from heavy residues. This can only be done under vacuum or in a steam distillation. 

Step 1 Make a new bond between a nucleophile and an electrophile Nucleophilic addition of the N-terminal amino group to the C=N bond of phenyl isothiocyanate gives a derivative of N-phenylthiourea. 

Edman Degradation (Section 27.4B) Treatment with phenyl isothiocyanate followed by acid removes the N-terminal amino acid as a substituted phenylthiohydan-toin, which is then separated and identified. The mechanism involves reaction of the electrophilic C atom of phenyl isothiocyanate with the nucleophilic terminal amino group to give an N-phenylthiourea intermediate that decomposes upon heating by cy-clization to give a thiazoKnone intermediate as the C-terminal peptide bond is cleaved. The thiazolinone intermediate isomerizes to the phenylthiohydantoin product. 

Instead of thiourea, N-phenylthiourea can also be used for the reaction with alkyl halogenides, and the S-alkyl-N-phenylthiuronium halo-genides formed can be converted to sharply melting picrates, picrolonates or styphnates (8). 

N-y4c. [1132-44-1]. N-[(Phenylammo)thioxomethyl acetamide, 9CI. N-Acetyl-N -phenylthiourea QHjoNjOS M 194.257... 

Cryst. (EtOH aq.). Mp 173°. l-N-Benzoyl [98095-85-3]. N-(Aminothioxomethyl)-N-phenylbenzamide, 9C1. 1 -Benzoyl-N-phenylthiourea CmHoNjOS M 256.328... 

N-Benzoyl [4921-82-8]. -[ Phenylamino)thioxomethyl benzamide, 9CI. i -Benzoyl-N -phenylthiourea CmHijNjOS M 256.328... 

V -(4-Bromopheny 1)- TV-hydroxy- N-phenylthiourea, B-00551 A -(4-Bromophenyl)-A-hydroxy-3-(2-thienyl)-2-propenamide, B-00552... 

---