3097-21-0

Usage

Uses

1,3-Dimethyl-1,3-dihydro-2H-benzimidazol-2-one is useful chemical in organic synthesis.

InChI:InChI=1/C9H10N2O/c1-10-7-5-3-4-6-8(7)11(2)9(10)12/h3-6H,1-2H3

Upstream product

• 4166-43-2 formic acid-(N-methyl-2-methylamino-anilide) 
• 7181-87-5 1,3-dimethylbenzimidazolium Iodide 
• 95-54-5 1,2-diamino-benzene 
• 616-38-6 carbonic acid dimethyl ester 
• 20691-72-9 4-iodo-2-nitroaniline 
• 865-47-4 potassium tert-butylate 
• 19163-21-4 5-phenylthiophene-2-carboxaldehyde 
• 500-22-1 3-pyridinecarboxaldehyde 
• 104-53-0 3-phenyl-propionaldehyde 
• 3226-39-9 1,4-dichloro-2-thiocyanatobenzene 
• 1571-08-0 methyl 4-formylbenzoate 
• 555-16-8 4-nitrobenzaldehdye 
• 105-07-7 4-cyanobenzaldehyde 
• 34036-07-2 3,4 difluorobenzaldehyde 

Downstream Products

• 55241-49-1 1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde 
• 1246685-15-3 5-[2-(2-chloro-4-methoxy-phenyl)-acetyl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one 
• 102477-68-9 4,6-dianilino-1,3-dimethyl-5,7-dinitro-1,3-dihydro-benzimidazol-2-one 
• 100881-95-6 5-anilino-1,3-dimethyl-4,6,7-trinitro-1,3-dihydro-benzimidazol-2-one 
• 24134-65-4 1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-sulfonyl chloride 

Relevant academic research and scientific papers

Revealing the unusual role of bases in activation/deactivation of catalytic systems: O-NHC coupling in M/NHC catalysis

Numerous reactions are catalyzed by complexes of metals (M) with N-heterocyclic carbene (NHC) ligands, typically in the presence of oxygen bases, which significantly shape the performance. It is generally accepted that bases are required for either substrate activation (exemplified by transmetallation in the Suzuki cross-coupling), or HX capture (e.g. in a variety of C-C and C-heteroatom couplings, the Heck reaction, C-H functionalization, heterocyclizations, etc.). This study gives insights into the behavior of M(ii)/NHC (M = Pd, Pt, Ni) complexes in solution under the action of bases conventionally engaged in catalysis (KOH, NaOH, t-BuOK, Cs2CO3, K2CO3, etc.). A previously unaddressed transformation of M(ii)/NHC complexes under conditions of typical base-mediated M/NHC catalyzed reactions is disclosed. Pd(ii) and Pt(ii) complexes widely used in catalysis react with the bases to give M(0) species and 2(5)-oxo-substituted azoles via an O-NHC coupling mechanism. Ni(NHC)2X2 complexes hydrolyze in the presence of aqueous potassium hydroxide, and undergo the same O-NHC coupling to give azolones and metallic nickel under the action of t-BuOK under anhydrous conditions. The study reveals a new role of NHC ligands as intramolecular reducing agents for the transformation of M(ii) into ligandless M(0) species. This demonstrates that the disclosed base-mediated O-NHC coupling reaction is integrated into the catalytic M/NHC systems and can define the mechanism of catalysis (molecular M/NHC vs. NHC-free cocktail-type catalysis). A proposed mechanism of the revealed transformation includes NHC-OR reductive elimination, as implied by a series of mechanistic studies including 18O labeling experiments.

FLUOROALKYLATING AGENT

Problem to be Solved It is intended to provide an industrially preferable fluoroalkylating agent and use thereof. Solution The present invention provides a fluoroalkylating agent represented by the general formula (1) wherein R1 is a C1 to C8 fluoroalkyl group; R2 and R3 are each independently a C1 to C12 alkyl group or the like; Y1 to Y4 are each independently a hydrogen atom, a halogen atom, or the like; and X? is a monovalent anion. A compound of the general formula (3): R4—S—R1 having an introduced C1 to C8 fluoroalkyl group is easily obtained by reacting a compound of the general formula (2): R4—S—Z wherein R4 is a hydrocarbon group or the like; and Z is a leaving group, with the compound of the general formula (1).

Copper-catalyzed efficient synthesis of a 2-benzimidazolone scaffold from 2-nitroaniline and dimethyl carbonate via a hydrosilylation reaction

This work reports a copper-catalyzed novel protocol for the tandem synthesis of 2-benzimidazolone derivatives from dimethyl carbonate (DMC) and various 2-nitroanilines by using polymethylhydrosiloxane (PMHS) as an inexpensive, stable and environmentally benign reducing agent. This methodology is applicable for the preparation of a broad range of biologically active 2-benzimidazolone derivatives with a good scope in good to excellent yields.

Carbonylation of o-phenylenediamine and o-aminophenol with dimethyl carbonate using lead compounds as catalysts

Lead compounds are active catalysts for carbonylation and carbonylation/methylation of o-phenylenediamine and o-aminophenol with dimethyl carbonate (DMC). 2-Benzimidazolone was obtained in 84% yield by the reaction of o-phenylenediamine with DMC for 1 h at 443 K in the presence of Pb(NO3)2. In the presence of Pb(OAc)2, the reaction quantitatively gave 1,3-dimethyl-2-benzimidazolone, which was formed by methylation of the primary product, 2-benzimidazolone, at 473 K. The effects of reaction variables on the yields of 2-benzimidazolone and 1,3-dimethyl-2-benzimidazolone were examined. The reaction of o-aminophenol with DMC selectively gave a carbonylation product, 2-benzoxazolone, or a carbonylation/methylation product, 3-methyl-2-benzoxazolone, depending on the reaction conditions in the presence of Pb(OAc)2.