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Synthesis and crystal structure of ethyl benzimidazole‐2‐yl phosphonate
Author(s) -
Hu FangZhong,
Zou XiaoMao,
Yang HuaZheng,
Weng LinHong
Publication year - 2000
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20000180524
Subject(s) - chemistry , phosphonate , benzimidazole , monoclinic crystal system , crystal structure , recrystallization (geology) , medicinal chemistry , hydrolysis , stereochemistry , crystallography , organic chemistry , paleontology , biology
When N ‐cyanoimido‐( O,O ‐diethyl)phosphonyl/ S ‐methyl thiocarbonate (1) was treated with o ‐phenylenediamine in the presence of Et 3 N in ethanol, diethyl benzimidazole‐2‐yl phosphonate (2) was obtained and hydrolyzed during the recrystallization in MeOH/H 2 O, generating ethyl benzimidazole‐2‐yl phosphonate (3). The crystal structure of compound 3 was determined by X‐ray diffraction method. The crystals belong to monoclinic, space group C 2 /c, a = 1.78406(18), b = 0. 83725(9), c= 1.67401(18) nm, β= 118.997(2)°, V = 2. 1870(4) nm 3 Z = 8, D c = 1.374 g/cm 3 , F (000) = 944. The final R and w R are 0.0499 and 0.1436, respectively. The mechanism of the above reaction is also discussed.