4104-75-0

Usage

Uses

Used in Chemical Synthesis:
N-METHYL-N-PHENYLTHIOUREA is used as a chemical intermediate for the production of S-Ethyl-N-methyl-N-phenyl-isothiourea, a compound with potential applications in various fields.
Used in Laboratory Applications:
In the presence of solvent acetone, N-METHYL-N-PHENYLTHIOUREA can be heated to produce hydriodide, which may have specific uses in laboratory settings or chemical research.

InChI:InChI=1/C8H10N2S/c1-10(8(9)11)7-5-3-2-4-6-7/h2-6H,1H3,(H2,9,11)

Upstream product

• 18773-77-8 methyl(phenyl)cyanamide 
• 4949-94-4 1-benzoyl-3-methyl-3-phenylthiourea 
• 14327-09-4 N-Methyl-N-phenyl-N'-(tert.-butyl)-thioharnstoff 
• 40398-25-2 1-Methyl-1-phenyl-3-ethoxycarbonylthioharnstoff 
• 66365-41-1 triphenylphosphine-thiocyanogen 
• 100-61-8 N-methylaniline 
• 124-41-4 sodium methylate 
• 55246-66-7 Imidazole-1-carbothioic acid methyl-phenyl-amide 
• 6544-02-1 silicon tetraisothiocyanate 
• 333-20-0 potassium thioacyanate 
• 74734-11-5 1H-imidazole-1-carbodithioic acid methyl ester 
• 532-55-8 Benzoyl isothiocyanate 

Downstream Products

• 82627-81-4 1-Methyl-3-phenyl-imidazolidin-4,5-dion-2-thion 
• 20495-97-0 methyl-(3-phenyl-thiazolidin-2-ylidene)-amine 
• 103765-60-2 2-(N-methyl-N-phenylamino)-4-phenylthiazole 
• 40699-64-7 N,S-dimethyl-N-phenyl-isothiourea 
• 69859-12-7 C₁₁H₁₈N₂SSi 
• 13163-11-6 2-(N-methyl-anilino)-thiazole-4,5-dione 
• 67754-09-0 N-Methyl-N-phenyl-S-tert.-butylisothiocarbamide 
• 51580-78-0 2-(N-methyl-anilino)-5-phenyl-thiazol-4-one 
• 86869-55-8 C₉H₁₀N₂OS 
• 118134-25-1 5-acetyl-4-methyl-2-(N-methylanilino)thiazole 
• 87944-02-3 ethyl 4-methyl-2-(N-methyl-N-phenylamino)thiazole-5-carboxylate 
• 93832-52-1 5-benzoyl-4-methyl-2-(N-methyl-N-phenylamino)thiazole 
• 111753-03-8 1-{2-[N-methyl(phenyl)amino]-4-phenyl-1,3-thiazol-5-yl}ethanone 
• 119476-63-0 C₁₃H₁₁⁽²⁾H₃N₂OS 

Relevant academic research and scientific papers

COMPOSITIONS AND METHODS FOR MODULATING A KINASE

The invention relates to compounds and methods for modulating one or more components of a kinase signaling cascade

Sultam thioureas: Synthesis and antiviral activity against west nile virus

The syntheses of eleven sultam thioureas, including nine new compounds, are described. These compounds were synthesized from thioureas and include the first sultam thioureas in which the two thiourea nitrogen groups are not identical. In addition, the first X-ray crystal structures of sultam thioureas and the antiviral activity of these compounds against West Nile virus (WNV) are reported. Georg Thieme Verlag Stuttgart New York.

ION CHANNEL MODULATORS

The present teachings provide carboxylic amide compounds that can modulate the activity of ion channels in a mammal. The present teachings also provide processes for producing said compounds and their pharmaceutically acceptable salts, hydrates and esters, and methods of treating a pathological condition or disorder, or alleviating a symptom thereof, using said compounds including their pharmaceutically acceptable salts, hydrates and esters. The compounds can be useful in modulating ion channel activity including treating a variety of conditions associated with the abnormal modulation of one or more voltage-gated calcium channels.

A convenient and efficient method for the synthesis of mono- and N,N-disubstituted thioureas

A convenient method for the synthesis of mono- and N,N-disubstituted thioureas by the debenzoylation of N-substituted- and N,N-disubstituted- N′-benzoylthioureas with hydrazine hydrate under solvent-free conditions has been developed. N-Substituted-N′-benzoylthioureas and hydrazine hydrate were mixed, and stirred at room temperature without a solvent to give the corresponding N-substituted thioureas in high yields.

1-(Methyldithiocarbonyl)imidazole: A useful thiocarbonyl transfer reagent for synthesis of substituted thioureas

1-(Methyldithiocarbonyl)imidazole 1 and its N-methyl quaternary salt 2 have been shown to be efficient methyldithiocarbonyl and thiocarbonyl transfer reagents for the synthesis of dithiocarbamates, symmetrical and unsymmetrical mono-, di- and tri-substituted thioureas in high yields under mild and simple non-hazardous reaction conditions. (C) 2000 Elsevier Science Ltd.

Substituted N-phenylisothioureas: Potent inhibitors of human nitric oxide synthase with neuronal isoform selectivity

S-Ethyl N-phenylisothiourea (4) has been found to be a potent inhibitor of both the human constitutive and inducible isoforms of nitric oxide synthase. A series of substituted N-phenylisothiourea analogues was synthesized to investigate the structure-activity relationship of this class of inhibitor. Each analogue was evaluated for human isoform selectivity. One analogue, S-ethyl N-[4-(trifluoromethyl)phenyl]isothiourea (39), exhibited 115-fold and 29-fold selectivity for the neuronal isoform versus the inducible and endothelial derived constitutive isoforms, respectively. Studies have shown the substituted N-phenylisothiourea 39 binds competitively with L,-arginine.

Activation of Dithiocarbamate by 2-Halothiazolium Salts

Activation of dithiocarbamate salts with 2-halo-3-alkyl-4-phenylthiazolium salt and subsequent one-pot nucleophilic reaction with N, S, and O nucleophiles provided substituted thioureas, dithiocarbamates, and thiocarbamates or amides, respectively, under very mild conditions.A useful thiocarbonyl-transfer reaction is also described that consists of activation of imidazolodithiocarbamate and a subsequent one-pot nucleophilic reaction. (Thiocarbonyl)diimidazole is generated in situ.

KINETICS AND MECHANISM OF REARRANGEMENT AND METHANOLYSIS OF ACYLPHENYLTHIOUREAS

S-Acyl-1-phenylthioureas and their 3-methyl derivatives are rearranged to 1-acyl derivatives of thiourea in methanolic solution.The rearrangement of the 1-acyl-1-phenyl derivative to the thermodynamically more stable 3-acyl derivative is subject to specific base catalysis.The rearrangement of acetyl group is about 2 orders of magnitude slower than that of benzoyl group. 1-Acetyl-1-phenylthiourea undergoes base-catalyzed methanolysis (giving phenylthiourea and methyl acetate) instead of the rearrangement.The methanolysis rates of 1-acyl-3-phenylthioureas and their N-methyl derivatives have been measured.The acetylthioureas react at most 3 x faster than the benzoyl derivatives.The methyl group at the nitrogen adjacent to acyl group accelerates the solvolysis by almost 2 orders of magnitude; the methyl group at the other nitrogen atom retards the solvolysis by almost 1 order of magnitude.Replacement of hydrogen atom by methyl group at the phenyl-substituted nitrogen increases acidity of the phenylacetylthiourea by 2 orders of magnitude.The same replacement at the benzoyl-substituted nitrogen increases the acidity by 3 orders of magnitude, the increase in the case of the acetyl derivative being as large as 4 orders of magnitude.

KINETICS AND MECHANISM OF METHANOLYSIS OF BENZOYL DERIVATIVES OF SUBSTITUTED PHENYLUREAS AND PHENYLTHIOUREAS

The methanolysis rate constants and dissociation constants have been measured of benzoyl derivatives of substituted phenylureas and phenylthioureas.The dissociation constants of the thio derivatives are higher by 1 order of magnitude and the rate constants are higher by 2 orders of magnitude than the respective values of the oxygen analogues.Logarithms of the rate and dissociation constants have been correlated with Hammett ? constant; the ρ constant of the methanolysis of the oxygen derivatives is almost 2 * higher than that of the thio derivatives, which is explained by a change in the rate-limiting step.Methylation of the phenyl nitrogen atom increases the acidity by almost 2 orders of magnitude.This effect is due obviously to steric hindrance to the conjugation with the adjacent carbonyl or thiocarbonyl group.

2-(N,N-Disubstituted Amino)thiazoles with Electron-withdrawing Groups at Position 5: Prepaeation and Investigation on Structural Features

A convenient procedure for preparing N-mono- and NN-di-substituted cyanamides from cyanogen bromide has been developed.N,N-Disubstituted thioureas, obtained from the cyanamides, were condensed with α-bromo-α-cyanoketones to give 5-cyano-2-(N,N-disubstituted amino)thiazoles and with α-bromo-ketones to give 2-(N,N-disubstituted amino)thiazoles.Substitution in the latter products afforded 5-trifluoroacetyl- and 5-nitro-2-(N,N-disubstituted amino)thiazoles; nitration is greatly facilitated by the presence of a 4-aryl group.The average values of the barriers of rotation of the barriers to rotation of the 2-NR2 groups (ΔG298) in the 5-substituted thiazoles were established by variable temperature 1H n.m.r. spectrometry to be 57.4 kJ mol -1 (5-NO2), 56.2 (5-COCF3), and 51.5 (5-CN).I.r. examination showed that the 5-trifluoroacetyl compounds adopt one rotational form preferentially; this is probably the carbonyl O,S-syn-conformation.