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
• Article Data: 11

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 
• 182936-41-0 O-(2-methoxy-6-methyl)phenyl N,N-diethylcarbamate 
• 244770-99-8 diethyl-carbamic acid 2-bromo-6-methoxy-phenyl ester 
• 858647-47-9 2-methoxy-3-nitrophenyl N,N-diethylcarbamate 
• 1160707-77-6 2-(N,N-diethylcarbamoyloxy)-3-methoxyphenylboronic acid 
• 81693-79-0 2-n-hexyl-1-methoxybenzene 
• 703-98-0 1-(2-hydroxy-3-methoxyphenyl)ethanone 
• 10040-93-4 1-(2-methoxyphenyl)-imidazole 

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

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.

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.