4-氨基-1-(4-氯苯基)-1H-5-咪唑羧酸乙酯 | 62382-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-氨基-1-(4-氯苯基)-1H-5-咪唑羧酸乙酯
• 英文名称: 4-amino-1-(4-chlorophenyl)-1H-5-imidazolecarboxylic acid ethyl ester
• 英文别名: 5-amino-3-(4-chloro-phenyl)-3H-imidazole-4-carboxylic acid ethyl ester；Ethyl 4-amino-1-(4-chlorophenyl)-1H-imidazole-5-carboxylate；ethyl 5-amino-3-(4-chlorophenyl)imidazole-4-carboxylate
• CAS: 62382-52-9
• 化学式: C₁₂H₁₂ClN₃O₂
• 分子量: 265.699
• InChiKey: LFBXLVXYXXHWHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  123-125 °C(Solv: ethanol (64-17-5))
• 沸点：
  439.2±35.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氨基-1-(4-氯苯基)-1H-5-咪唑羧酸乙酯 在 乙醇 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 生成 [1-(4-chlorophenyl)-7-oxo-6,7-dihydroimidazo[4,5-d]pyrimidin-5-ylsulfanyl]acetic acid ethyl ester
  参考文献：
  名称：

  New Syntheses of 2-Alkylthio-4-oxo-3,4-dihydroquinazolines, 2 - Alkylthio - quinazolines, as well as Their Hetero Analogues

  摘要：

  N-Chloroacetylanthranilic acid ethyl ester reacts with potassium thiocyanate in the presence of alcohol to give the (4-oxo-3,4-dihydroquinazolin-2-yl-sulfanyl)acetic acid ester (3a). In the presence of water or amines the acetic acid derivative (3b) or the acetamide derivatives (3c,d) are obtained. 2-Amino-di-oxo-3,4-dihydroquinazolines (4) arise if vigorous reaction conditions are employed. Analogously, N-chloroacetyl derivatives of 5-membered heterocycles with enaminocarbonyl structure (5, 7, 9, 11, 13, 20, 23) react with potassium thiocyanate to yield thieno[2,3-d]-, thieno[3,2-d]-, imidazo[4,5-d]-, pyrrolo[3,2-d]-, and thiazolo[4,5-d]pyrimidines (6, 8, 10, 12, 14, 21, 24). Quinazolines (18, 19) are formed from the reaction of 2-chloroacetylaminoacetophenone (16a) and 2-chloroacetylaminobenzophenone (16b) with potassium thiocyanate and subsequent treatment of the intermediates with. amines.

  DOI：

  10.3987/com-00-8954

文献信息

• Verkoyen, Carl; Golovinsky, Evgeny; Mueller, Gunther, Liebigs Annalen der Chemie, 1987, p. 957 - 960
  作者：Verkoyen, Carl、Golovinsky, Evgeny、Mueller, Gunther、Koelbel, Margit、Norpoth, Klaus

  DOI：——

  日期：——
• Phosphorus pentoxide in organic synthesis-I
  作者：F.E. Nielsen、E.B. Pedersen

  DOI：10.1016/0040-4020(82)80226-3

  日期：1982.1
• NIELSEN, F. E.;PEDERSEN, E. B., TETRAHEDRON, 1982, 38, N 10, 1435-1441
  作者：NIELSEN, F. E.、PEDERSEN, E. B.

  DOI：——

  日期：——
• VERKOYEN, CARL;GOLOVINSKY, EVGENY;MULLER, GUNTHER;KOLBEL, MARGIT;NORPOTH,+, LIEBIGS ANN. CHEM.,(1987) N 11, 957-960
  作者：VERKOYEN, CARL、GOLOVINSKY, EVGENY、MULLER, GUNTHER、KOLBEL, MARGIT、NORPOTH,+

  DOI：——

  日期：——
• New Syntheses of 2-Alkylthio-4-oxo-3,4-dihydroquinazolines, 2 - Alkylthio - quinazolines, as well as Their Hetero Analogues
  作者：Margit Gruner、Matthias Rehwald、Katrin Eckert、Karl Gewald

  DOI：10.3987/com-00-8954

  日期：——

  N-Chloroacetylanthranilic acid ethyl ester reacts with potassium thiocyanate in the presence of alcohol to give the (4-oxo-3,4-dihydroquinazolin-2-yl-sulfanyl)acetic acid ester (3a). In the presence of water or amines the acetic acid derivative (3b) or the acetamide derivatives (3c,d) are obtained. 2-Amino-di-oxo-3,4-dihydroquinazolines (4) arise if vigorous reaction conditions are employed. Analogously, N-chloroacetyl derivatives of 5-membered heterocycles with enaminocarbonyl structure (5, 7, 9, 11, 13, 20, 23) react with potassium thiocyanate to yield thieno[2,3-d]-, thieno[3,2-d]-, imidazo[4,5-d]-, pyrrolo[3,2-d]-, and thiazolo[4,5-d]pyrimidines (6, 8, 10, 12, 14, 21, 24). Quinazolines (18, 19) are formed from the reaction of 2-chloroacetylaminoacetophenone (16a) and 2-chloroacetylaminobenzophenone (16b) with potassium thiocyanate and subsequent treatment of the intermediates with. amines.