preparation and application of 2-bromobenzyl-n-succinimidyl carbonate_industrial additives

preparation and application background and overview of 2-bromobenzyl-n-succinimidyl carbonate

2-bromobenzyl-n-succinimidyl carbonate is an organic intermediate that can be prepared in one step from 2-bromobenzyl alcohol and n,n’-disuccinimidyl carbonate.

preparation and application of 2-bromobenzyl-n-succinimidyl carbonate

to a solution of 2-bromobenzyl alcohol (2.83 g, 15.0 mmol, 1.0 equiv) and dmap (916 mg, 7.5 mmol, 0.5 equiv) in mecn/dcm 1:1 (45 ml) was added n,n ‘-disuccinimidyl carbonate (3.84 g, 15.0 mmol, 1.0 equiv). the mixture was continuously stirred at room temperature for 18 hours. the mixture was washed with h₂o (1×45ml), saturated nahco₃, sodium chloride solution (1×45ml), and washed with mgso₄dry, filter and concentrate in vacuo. the residue was recrystallized from iproh to give 2-bromobenzyl-n-succinimidyl carbonate. c12h10no5br, mw = 328.12. lc-ms 3: t_r = 0.82 min.

preparation and application of 2-bromobenzyl-n-succinimidyl carbonate

2-bromobenzyl-n-succinimidyl carbonate can be used to efficiently convert amines into protected guanidines.

dissolve s-methylisothiourea sulfate (1.51 g, 5.43 mmol) in h₂o (16 ml) and add dioxane (14 ml) and 1m aqueous naoh (11 ml, 11 mmol), then 2-bromobenzyl-n-succinimidyl carbonate (14.27 g, 43.5 mmol, 2 equiv) was added. the reaction mixture was stirred at room temperature for 24 hours, then concentrated under reduced pressure. the residue was dissolved in etoac (150 ml), and washed with 10% citric acid aqueous solution (3×30 ml) and saturated nahco₃ aqueous solution. , dried (mgso₄) and evaporated, the solid residue was recrystallized from etoh to give the product. yield 7.42 g, 70%. mp 101-103 °c. ¹h nmr (200 mhz, cd synthesis of fluorphlogopite cl3): δ = 2.45 (s, 3 h), 5.29 (s, 2 h), 5.31 (s, 2 h), 7.15-7.61 (m, 8 h), 11.89 (s, 1 h). ^{13 lithium metaborate}c nmr (50 mhz, cdcl₃): δ = 14.71, 67.43, 67.84, 122.93, 123.70, 127.54, 127.64, 129.34, 129.61, 130.28, 130.35, 132.77, 132.98, 134.01, 13 5.10, 151.35, 160.85, 173.25. anal. calcd for c18h16br2n2o4s: c, 41.88; h, 3.12; n, 5.43; br, 30.96. found: c, 42.01; h, 3.01; n, 5.41; br, 30.99.

references

[1] [chinese invention, chinese invention authorization] cn201180030390.1 1-phenyl-substituted heterocyclic derivatives and their use as prostaglandin d2 receptor modulators

[2] gers t , kunce d , markowski p , et al. reagents for efficient conversion of amines to guanidines. (p)[j]. cheminform, 2010, 35(17).