6780-39-8

Basic information

• Product Name: Benzenecarboximidic acid, N-phenyl-, methyl ester
• CAS NO: 6780-39-8
• Molecular Formula: C14H13NO
• Molecular Weight: 211.263
• Mol File: 6780-39-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Benzenecarboximidic acid, N-phenyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenecarboximidic acid, N-phenyl-, methyl ester(6780-39-8)
• EPA Substance Registry System: Benzenecarboximidic acid, N-phenyl-, methyl ester(6780-39-8)

Safety Data

• Hazardous Substances Data: 6780-39-8(Hazardous Substances Data)

Upstream product

• 4686-14-0 2-phenyl-2-(phenylimino)acetonitrile 
• 124-41-4 sodium methylate 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 67-56-1 methanol 
• 151-50-8 potassium cyanide 
• 201024-81-9 C,N-diphenylnitrone 
• 87775-63-1 3,5-dichlorophenyl N-phenylbenzimidate 
• 100-52-7 benzaldehyde 
• 5873-86-9 methyl thiobenzoate 
• 622-37-7 Phenyl azide 
• 93-98-1 N-phenyl benzoyl amide 
• 74-88-4 methyl iodide 
• 62-53-3 aniline 
• 707-07-3 orthobenzoic acid trimethyl ester 

Downstream Products

• 1934-92-5 N-methyl-N-phenyl-benzamide 
• 93-98-1 N-phenyl benzoyl amide 
• 74-87-3 methylene chloride 
• 574-45-8 N-(diphenylmethylidene)phenylamine 
• 93-58-3 benzoic acid methyl ester 
• 62-53-3 aniline 

Relevant articles and documents

Indium-mediated one-pot synthesis of benzoxazoles or oxazoles from 2-nitrophenols or 1-aryl-2-nitroethanones

One-pot reduction-triggered heterocyclizations from 2-nitrophenols to benzoxazoles and from 1-aryl-2-nitroethanones to oxazoles were investigated. In the presence of indium/AcOH in benzene at reflux, 2-nitrophenols and R-C(OMe)3 (R=H, Me, Ph) produced excellent yields of corresponding benzoxazoles within an hour. Similarly, 1-aryl-2-nitroethanones and Ph-C(OMe)3 in the presence of indium/AcOH in acetonitrile transformed into the corresponding oxazoles with good yields.

115. 1,3-Dipole mit Zentralem S-Atom aus der Umsetzung von Aziden mit Thiocarbonyl-Verbindungen: Eine unerwartete MeS-Wanderung im Abfangprodukt eines 'Thiocarbonyl-aminids' mit Dithiobenzoesaeure-methylester

Reaction of PhN3 with O-methyl thiobenzoate (11a) and thioacetate (11c) as well as with the dithio esters 11b, d at 80 deg C yields the corresponding imidates and thioimidates 12 (Scheme 3).The formation of 12 is rationalized by a 1,3-dipolar cycloaddition of the azide and the C=S group followed by successive elimination of N2 and S.In the three-component reaction of 11b, PhN3, and the sterically crowded thioketone 1a, 1,2,4-trithiolane 13a and 1,4,2-dithiazolidine 3a are formed in addition to 12b (Scheme 4).The heterocycles 13 and 3a are trapping products of 1a and 'thiocarbonyl-aminide' 5a and 'thiocarbonyl-amidine' 2a (Ar= Ph), respectively (Scheme 6).These 1,3-dipoles are formed as reactive intermediates.Surprisingly, in the presence of catalytic amounts of acids, the major product is the (methyldithio)cyclobutyl thioimidate of type 14 (Scheme 5), formed by an acid-catalyzed MeS migration in dithiazolidine 17.A reaction mechanism is proposed in Scheme 7.

Mechanisms of Nucleophilic Attack at Carbon-Nitrogen Double Bonds. The Reaction of Aryl N-Arylbenzimidates with Methoxide Ion

Rate data for the reaction of three series of aryl N-arylbenzimidates with methoxide ion at 303 K are presented.Linear Hammett plots were obtained for each series.Solvent isotope effects have also been measured.The results are interpreted in terms of rate-determining formation of a tetrahedral intermediate, irrespective of the nature of the substituent.