85630-19-9

Basic information

• Product Name: N,N-diethyl-1-carbamyloxy-2-methoxybenzene
• Synonyms: N,N-diethyl-1-carbamyloxy-2-methoxybenzene
• CAS NO: 85630-19-9
• Molecular Weight: 223.272
• Mol File: 85630-19-9.mol

Chemical Properties

• CAS DataBase Reference: N,N-diethyl-1-carbamyloxy-2-methoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-diethyl-1-carbamyloxy-2-methoxybenzene(85630-19-9)
• EPA Substance Registry System: N,N-diethyl-1-carbamyloxy-2-methoxybenzene(85630-19-9)

Safety Data

• Hazardous Substances Data: 85630-19-9(Hazardous Substances Data)

Upstream product

• 88-10-8 N,N-diethylcarbamyl chloride 
• 90-05-1 2-methoxy-phenol 

Downstream Products

• 19351-20-3 N,N-diethyl-2-hydroxy-3-methoxybenzamide 
• 10040-93-4 1-(2-methoxyphenyl)-imidazole 
• 703-98-0 1-(2-hydroxy-3-methoxyphenyl)ethanone 
• 81693-79-0 2-n-hexyl-1-methoxybenzene 
• 27347-13-3 N-(2-methoxyphenyl)morpholine 
• 1160707-77-6 2-(N,N-diethylcarbamoyloxy)-3-methoxyphenylboronic acid 

Relevant articles and documents

Application of directed metalation in synthesis. Part 6: A novel anionic rearrangement under directed metalation conditions leading to heteroannulation

A short and efficient synthesis of condensed 1,4-oxathiin-2-ones from easily available phenols is described. The key step in this synthesis is a hitherto unreported anionic rearrangement under directed metalation conditions. The rearrangement occurs after

N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C-O bond activation enabled by a reusable and durable nickel(0) catalyst

An effective and general aryl amination protocol has been developed using a magnetically recoverable Ni(0) based nanocatalyst. This new stable catalyst was prepared on Fe3O4@SiO2 modified by EDTA and investigated by FT-IR, EDX, TEM, XRD, DLS, FE-SEM, XPS, NMR, TGA, VSM, ICP and elemental analysis techniques. The reaction proceeded via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles with good to excellent yields. Furthermore, the catalyst could be easily recovered by using an external magnetic field and directly reused at least six times without notable reduction in its activity. This journal is

Experimental and computational study of the 1,5-o → n carbamoyl snieckus-fries-type rearrangement

The reactions of o-lithiated O-aryl N,N-diethylcarbamates with different C-N multiple bond electrophiles have been thoroughly studied. A 1,5-O → N carbamoyl shift, a new variation of the anionic Fries-type rearrangement, takes place when nitriles, imines, or alkylcarbodiimides are employed. In these cases, the carbamoyl group plays a dual role as a directing group, building up a variety of functional groups through the 1,5-O → N carbamoyl migration. On the other hand, the use of iso(thio)cyanates and arylcarbodiimides led to non-rearranged o-functionalized Oarylcarbamates. This reactivity was further computationally explored, and the governing factor could be traced back to the relative basicity of the alternative products (migrated vs nonmigrated substrates). This exploration also provided interesting insights about the degree of complexation of the lithium cations onto these substrates. A new access to useful 2-hydroxybenzophenone derivatives has also been developed.

Directed ortho-Metalation of Aryl Amides, O-Carbamates, and Methoxymethoxy Systems: Directed Metalation Group Competition and Cooperation

A systematic study on the competitive metalation of derivatives containing four directed metalation groups (DMGs), namely, Cl, OMe, methoxymethoxy (OMOM), and CONEt2, in comparison with the OCONEt2 DMG is described. In addition, the

1,5-O → N Carbamoyl Snieckus-Fries-Type Rearrangement

The reaction of o-lithiated O-aryl N,N-diethylcarbamates with (hetero)aromatic nitriles gives rise to functionalized salicylidene urea derivatives in high yields through a new 1,5-O → N carbamoyl migration. This Snieckus-Fries-type rearrangement nicely complements previously known O → C and O → O related shifts. In addition, when dimethylmalononitrile is used as the electrophilic partner, the carbamoyl shift is preferred over the expected transnitrilation reaction.

Highly enantioselective (-)-sparteine-mediated lateral metalation-functionalization of remote silyl protected ortho -ethyl N, N -dialkyl aryl O -carbamates

We report the enantioselective, lateral deprotonation of ortho-protected or functionalized tertiary N,N-dialkyl aryl O-carbamates 5-7 (Scheme 2) and meta-protected carbamates 14, 15, and 20 (Schemes 5 and 7) by s-BuLi/(-)-sparteine and subsequent quench w

Lithiation of a silyl ether: Formation of an ortho-fries hydroxyketone

A hydroxy-directed alkylation of an N,N-diethylarylamide using CIPE-assisted α-silyl carbanions (CIPE=complex-induced proximity effect) has been developed using a simple reagent combination of LDA (lithium diisopropylamide) and chlorosilane. A study of the mechanism, and the application of the procedure to an anionic Snieckus-Fries rearrangement for a highly efficient synthesis of the potent phosphatidylinositol 3-kinase (PI3K) inhibitor LY294002, are reported.

Application of directed metalation in synthesis. Part 5:1,2 Synthesis of condensed sulfur-oxygen heterocycle via novel anionic rearrangement-cyclisation

Introduction of the methyl sulfanyl function in the ortho-position to O-carbamate functionality under standard directed metalation condition was followed by side-chain deprotonation with sec-butyl lithium at -78 °C. Upon warming to room temperature, the d

Application of directed metallation in synthesis. Part 3: Studies in the synthesis of (±)-semivioxanthin and its analogues

The synthesis of several analogues of (±)-semivioxanthin including five thiophene analogues, using directed metalation are reported. The strategy consisted of the synthesis of functionalized naphthalene or benzo[b]thiophene as building blocks followed by

New syntheses of the benzoquinone primin and its water-soluble analog primin acid via Heck reactions

The syntheses of primin, 2-methoxy-6-pentylbenzoquinone (1), a major allergen of Primula obconica, and its water-soluble acid analog primin acid (2) are reported. The key steps were ortho-lithiation reactions of protected hydroquinones, palladium coupling (Heck) reactions, and salcomine-catalyzed oxidations of phenols to quinones.