Synthesis and crystal structure of ethyl benzimidazole-2-yl phosphonate

• 作 者: 胡方中 邹小毛 杨华铮 翁林红
• 机 构: State Key Laboratory of Elemento-Organic Chemistry,Institute of Ekmento-Organic Chemistry,Nankai Uni
• 出 处: Chinese Journal of Chemistry
• 发表日期: 2000年05期
• 关键词: phosphonate hydrolyzed monoclinic diethyl heterocyclic antibacterial generating

When N-cyanoimido-( O,O-diethyl)phosphonyl/S-methyl thiocarbonate (1) was treated with o-phenylenediamine in the presence of Et3N in ethanol,diethyl benzimidazole-2-yl phos-phonate (2) was obtained and hydrolyzed during the recrys-tallization in MeOH/H2O,generating ethyl benzimidazole-2-yl phosphonate (3).Hie crystal structure of compound 3 was determined by X-ray diffraction method.The crystals belong to monoclinic,space group C2/c,a = 1.78408(18) ,6 = 0.83725(9),c= 1.67401(18) nm,β= 118.997(2),V = 2.1870(4) nm3,Z = 8,Dc=1.374 g/cm3,F(000)=944.The final R and wR are 0.0499 and 0.1436,respectively.The mechanism of the above reaction is also discussed.

When N-cyanoimido- (O, O-diethyl) phosphonyl / S-methyl thiocarbonate (1) was treated with o-phenylenediamine in the presence of Et3N in ethanol, diethyl benzimidazole- 2-yl phos-phonate hydrolyzed during the recrys-tallization in MeOH / H2O, generating ethyl benzimidazole-2-yl phosphonate (3) .Hie crystal structure of compound 3 was determined by X-ray diffraction method. The crystals belong to monoclinic, space group C2 / c, a = 1.78408 (18) 6 = 0.83725 (9) c = 1.67401 (18) nm β = 118.997 (2) V = 2.1870 (4) nm3 Z = 8 Dc = 1.374 g / cm3 F 000) = 944. The final R and wR are 0.0499 and 0.1436, respectively. The mechanism of the above reaction is also discussed.