N,N-diethyl-4-methyl-N'-(tritylcarbamothioyl)benzimidamide | 1173243-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N,N-diethyl-4-methyl-N'-(tritylcarbamothioyl)benzimidamide
• CAS: 1173243-37-2
• 化学式: C₃₂H₃₃N₃S
• 分子量: 491.7
• InChiKey: NIQXBVOYRGCFDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.95
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  27.63
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-4-methyl-N'-(tritylcarbamothioyl)benzimidamide 在 盐酸羟胺 、 silver nitrate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-(4-tolyl)-N-trityl-1,2,4-oxadiazol-3-amine
  参考文献：
  名称：

  A Diversified Assembly of 1,2,4-Oxadiazol-3-amines: Metallic Thiophile Catalyzed Chemoselective One-Pot Reaction of Aryl Isothiocyanates, Amidines/Guanidines, and Hydroxylamine

  摘要：

  An efficient one-pot synthesis of 1,2,4-oxadiazol-3-amines from simple starting materials, isothiocyanates, amidines/guanidines, and hydroxylamine, is described. The reaction is facilitated by metallic-thiophile-assisted desulfurization of in situ formed amidino- or guanidinothiourea to give chemoselectively N-hydroxyguanidine intermediates that give exclusively various 1,2,4-oxadiazol-3-amines in good to excellent yields. The reaction mechanistic pathway may proceed through an intramolecular 5-exotrig cyclization.

  DOI：

  10.1055/s-0032-1317504
• 作为产物：
  描述：

  对甲苯腈 在 aluminum (III) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N,N-diethyl-4-methyl-N'-(tritylcarbamothioyl)benzimidamide
  参考文献：
  名称：

  A Diversified Assembly of 1,2,4-Oxadiazol-3-amines: Metallic Thiophile Catalyzed Chemoselective One-Pot Reaction of Aryl Isothiocyanates, Amidines/Guanidines, and Hydroxylamine

  摘要：

  An efficient one-pot synthesis of 1,2,4-oxadiazol-3-amines from simple starting materials, isothiocyanates, amidines/guanidines, and hydroxylamine, is described. The reaction is facilitated by metallic-thiophile-assisted desulfurization of in situ formed amidino- or guanidinothiourea to give chemoselectively N-hydroxyguanidine intermediates that give exclusively various 1,2,4-oxadiazol-3-amines in good to excellent yields. The reaction mechanistic pathway may proceed through an intramolecular 5-exotrig cyclization.

  DOI：

  10.1055/s-0032-1317504

文献信息

• A convenient synthesis of di- and trisubstituted 2-aminoimidazoles from 1-amidino-3-trityl-thioureas
  作者：Jitendra C. Kaila、Arshi B. Baraiya、Amit N. Pandya、Hitesh B. Jalani、Kamala K. Vasu、V. Sudarsanam

  DOI：10.1016/j.tetlet.2009.04.083

  日期：2009.7

  Convenient synthesis of 2-amino-1,5-disubstituted and 2-amino-1,4,5-trisubstituted imidazoles has been reported using readily available starting materials and simple reagents under mild conditions. Guanylation of 1-amidino-3-trityl-thioureas 1 and 7 using mercury(II) chloride (Caution) as a thiophile resulted in corresponding guanidines 2 and 8 which on reaction with alpha-bromo ketones yielded 2-tritylaminoimidazoles. Deprotection of 2-tritylaminoimidazoles using trifluoroacetic acid at room temperature furnished desired 2-aminoimidazoles 4 and 10 in good to moderate yields. (C) 2009 Elsevier Ltd. All rights reserved.