Electric Literature of 53844-02-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 53844-02-3, name is Benzyl (2-bromoethyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
According to the described general procedure (GP11), N-alkylation of commercially available 4(5)-methylimidazole (4.343 g ; 52.90 mmol) with (2-bromo-ethyl)-carbamic acid benzyl ester (15.019 g ; 58.19 mmol), and subsequent purification by FC (DCM /MeOH =10/1) afforded a mixture of [2-(4-methyl-imidazol-1-yl)-ethyl]-carbamic acid benzyl ester, and [2-(5-methyl-imidazol-1-yl)ethyl]-carbamic acid benzyl ester (ratio of regioisomers close to 1/1, according to 1H-NMR) as a yellow oil (4.270 g ; 31%). LC-MS: tR=0.68 min. (2 regioisomers); [M+H]+: 260.46 g/mol. A mixture of [2-(4-methyl-imidazol-1-yl)-ethyl]carbamic acid benzyl ester, [2-(5-methyl-imidazol-1-yl)-ethyl]-carbamic acid benzyl ester (1.198 g; 4.62 mmol; ratio of regioisomers close to 1/1, according to 1H-NMR), and 10% palladium on activated charcoal (240 mg; 20% in mass) was placed under nitrogen before addition of anh. MeOH (20 ml). The resulting mixture was placed under vacuum, and then under hydrogen (1 atm), and stirring at rt was continued for 2.5 h. Filtration over a pad of celite, concentration to dryness under reduced pressure afforded a mixture of 2-(4-methyl-imidazol-1-yl)-ethylamine, and 2-(5-methyl-imidazol-1-yl)-ethylamine as a slightly yellow oil (540 mg; 93%). LC-MS: tR=0.17 min. (2 regioisomers); [M+H]+: no ionisation. These primary amines were converted to the corresponding chlorhydrate salt by treatment of a solution of regioisomeric amines (540 mg ; 4.31 mmol) in dichloromethane (5 ml) with 4N HCl in 1,4-dioxane (3.25 ml ; 3 eq.). Concentration to dryness under reduced pressure afforded a beige solid which was further dried under HV.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Benzyl (2-bromoethyl)carbamate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; Aissaoui, Hamed; Boss, Christoph; Koberstein, Ralf; Siegrist, Romain; Sifferlen, Thierry; US2011/105514; (2011); A1;,
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