19009-45-1

Usage

Synthesis Reference(s)

Tetrahedron, 36, p. 539, 1980 DOI: 10.1016/0040-4020(80)80032-9

Upstream product

• 463-71-8 thiophosgene 
• 17890-34-5 N-(trimethylsilyl)phenyl(methyl)amine 
• 67-66-3 chloroform 
• 2739-12-0 N-methylaniline hydrochloride 
• 7732-18-5 water 
• 100-61-8 N-methylaniline 
• 36325-39-0 N-phenylthioacetamide 

Downstream Products

• 87463-11-4 O-methyl N-methyl-N-phenylcarbamothioate 
• 5076-39-1 N,N'-Dimethyl-N,N'-diphenylthioharnstoff 
• 100449-45-4 Tetrahydro-N-methyl-N-phenyl-2-thioxo-2H-1,3-thiazin-3-carboxamid 
• 100449-46-5 Tetrahydro-N-methyl-N-phenyl-2-oxo-2H-1,3-thiazin-3-thiocarboxamid 
• 100449-39-6 Tetrahydro-N-methyl-N-phenyl-2-thioxo-2H-1,3-thiazin-3-thiocarboxamid 
• 87531-20-2 1-(Diphenylphosphino)-N-methyl-N-phenylthioformamid 
• 10591-84-1 N,N’-dimethyl-N,N’-diphenylthiuram disulfide 
• 21076-09-5 2-methyl-4-phenyl-3-thiosemicarbazide 
• 1415351-59-5 (E)-O-but-2-enyl methyl(phenyl)carbamothioate 
• 1415351-67-5 S-but-3-en-2-yl methyl(phenyl)carbamothioate 
• 1558811-66-7 S-2-phenylbut-3-en-2-yl methylcarbamothioate 
• 219646-02-3 C₁₇H₁₄N₂O 
• 1265169-79-6 4-amino-5-fluoro-N-methyl-2-oxo-N-phenyl-pyrimidine-1(2H)-carbothioamide 
• 3012-99-5 methyl-phenyl-thiocarbamic acid S-methyl ester 

Relevant academic research and scientific papers

Tertiary thiols from allylic thiocarbamates by tandem enantioselective [3,3]-sigmatropic rearrangement and stereospecific arylation

The synthesis of tertiary thiols in enantiomerically enriched form is accomplished by lithiation of enantiomerically enriched N-aryl allylic thiocarbamates. Formation of an allyllithium derivative promotes intramolecular N to C aryl migration to the posit

S-allyl thiocarbamates from allylic alcohols by in situ [3,3]-sigmatropic rearrangement of a thiocarbonyldiimidazole adduct

Treatment of allylic alcohols with thiocarbonyldiimidazole generates an unstable O-allyl imidazolyl thione ester, which rearranges spontaneously and in high yield to the corresponding S-allyl imidazolyl thiol ester. Displacement of the imidazole by N-alky

Radical OfC transposition: A metal-free process for conversion of phenols into benzoates and benzamides

We report a metal-free procedure for transformation of phenols into esters and amides of benzoic acids via a new radical cascade. Diaryl thiocarbonates and thiocarbamates, available in a single high-yielding step from phenols, selectively add silyl radicals at the sulfur atom of the CdS moiety. This addition step, analogous to the first step of the Barton-McCombie reaction, produces a carbon radical which undergoes 1,2 OfC transposition through an O-neophyl rearrangement. The usually unfavorable equilibrium in the reversible rearrangement step is shifted forward via a highly exothermic C-S bond scission in the O-centered radical, which furnishes the final benzoic ester or benzamide product. The metal-free preparation of benzoic acid derivatives from phenols provides a potentially useful alternative to metal-catalyzed carbonylation of aryl triflates.

DIRECT CONVERSION OF PHENOLS INTO AMIDES AND ESTERS OF BENZOIC ACID

A method is provided for the preparation of an aromatic carboxylic acid aryl ester or an N-aryl aromatic carboxamide. The method comprises contacting an O,O-diaryl thiocarbonate or an O-aryl-N-aryl thiocarbamate with a reactant that regioselectively reacts with sulfur, which contact causes an O-neophyl rearrangement, thereby forming either the aromatic carboxylic acid aryl ester or the N-aryl aromatic carboxamide, respectively.

Novel [2-(4-piperidinyl)ethyl](thio)ureas: Synthesis and antiacetylcholinesterase activity

A series of 1-ar(o)yl-3-[2-(1-benzyl-4-piperidinyl)ethyl](thio)urea derivatives was synthesized and evaluated for antiacetylcholinesterase activity. Most aroyl(thio)urea derivatives showed potent inhibitory activity in the sub-micromolar range. A comparable potency was obtained with the aryl(thio)urea analogues by replacing the phenyl with a 2-pyridyl group. The substituted guanidine variations proved to be almost inactive whereas the nitroethylene analogues appeared to be quite efficient. These results were interpreted in terms of the preferential cis-trans conformation of the aroyl(thio)urea and 2-pyridyl(thio)urea moieties involving the existence of hydrogen bonding. In vivo experiments showed that compound 7m had maximal antiamnestic activity at 0.03 mg/kg with a therapeutic ratio greater than 1000, while cholinergic side effects were only seen at doses 100-fold the maximally effective antiamnestic dose. Compound 7m represents a potentially interesting antidementia agent.

A NEW SYNTHETIC PROCEDURE FOR THE CONVENIENT PREPARATION OF THIOCARBAMOYL CHLORIDES AND THE NOVEL BIS-THIOCARBAMOYL CHLORIDES

Treatment of N-silylamines with excess thiophosgene affords thiocarbamoyl chlorides in good yields and excellent purity.This method was also suitable for preparing the first bis-thiocarbamoyl chlorides from N,N'-bis(trimethylsilyl)-diamines.Bis-thiocarbam