5-N-methylcarbamoyl-3-phenyl-2,4-thiazolidinedione | 150455-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-N-methylcarbamoyl-3-phenyl-2,4-thiazolidinedione
• 英文别名: N-methyl-2,4-dioxo-3-phenyl-1,3-thiazolidine-5-carboxamide
• CAS: 150455-47-3
• 化学式: C₁₁H₁₀N₂O₃S
• 分子量: 250.278
• InChiKey: XMDDUCAFKGXWTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-N-methylcarbamoyl-3-phenyl-2,4-thiazolidinedione 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 反应 3.0h， 以49%的产率得到4-chloro-2-oxo-3-phenylthiazolidine-5-N-methylcarboxamide
  参考文献：
  名称：

  Study of Thiazolo[4,5-d]pyrimidines: The Synthesis of Thiazolo[4,5-d]pyrimidine-2,7-diones and Novel Ring Opening to 2,4-Thiazolidinedione

  摘要：

  Treatment of 7-oxo-3-phenylthiazolo[4,5-d]-pyrimidine-2(6H)-thione (1) with dimethyl sulfate afforded 6-methyl-3-phenylthiazolo[4,5-d]pyrimidine-2,7-dione (2), 3-phenylthiazolo[4,5-d]pyrimidine-2,7(6H)-dione (3) and/or 5-N-methylcarbamoyl-3-phenyl-2,4-thiazolidinedione (5), depending on reaction conditions. Furthermore, reaction of 3 with dimethyl sulfate caused the ring opening to give corresponding 5. Also, treatment of 5 with phosphorus oxychloride gave 4-chloro-2-oxo-3-phenylthiazolidine-5-N-methylcarboxamide (6).

  DOI：

  10.3987/com-92-6230
• 作为产物：
  描述：

  7-Oxo-3-phenylthiazolo<4,5-d>pyrimidin-2-thion 在 水 、 硫酸二甲酯 作用下， 反应 1.0h， 生成 5-N-methylcarbamoyl-3-phenyl-2,4-thiazolidinedione
  参考文献：
  名称：

  Study of Thiazolo[4,5-d]pyrimidines: The Synthesis of Thiazolo[4,5-d]pyrimidine-2,7-diones and Novel Ring Opening to 2,4-Thiazolidinedione

  摘要：

  Treatment of 7-oxo-3-phenylthiazolo[4,5-d]-pyrimidine-2(6H)-thione (1) with dimethyl sulfate afforded 6-methyl-3-phenylthiazolo[4,5-d]pyrimidine-2,7-dione (2), 3-phenylthiazolo[4,5-d]pyrimidine-2,7(6H)-dione (3) and/or 5-N-methylcarbamoyl-3-phenyl-2,4-thiazolidinedione (5), depending on reaction conditions. Furthermore, reaction of 3 with dimethyl sulfate caused the ring opening to give corresponding 5. Also, treatment of 5 with phosphorus oxychloride gave 4-chloro-2-oxo-3-phenylthiazolidine-5-N-methylcarboxamide (6).

  DOI：

  10.3987/com-92-6230

文献信息

• Study of Thiazolo[4,5-d]pyrimidines: The Synthesis of Thiazolo[4,5-d]pyrimidine-2,7-diones and Novel Ring Opening to 2,4-Thiazolidinedione
  作者：Katsuhiko Nagahara、Masae Sekine、Atsushi Takada、Howard B. Cottam、Roland K. Robins

  DOI：10.3987/com-92-6230

  日期：——

  Treatment of 7-oxo-3-phenylthiazolo[4,5-d]-pyrimidine-2(6H)-thione (1) with dimethyl sulfate afforded 6-methyl-3-phenylthiazolo[4,5-d]pyrimidine-2,7-dione (2), 3-phenylthiazolo[4,5-d]pyrimidine-2,7(6H)-dione (3) and/or 5-N-methylcarbamoyl-3-phenyl-2,4-thiazolidinedione (5), depending on reaction conditions. Furthermore, reaction of 3 with dimethyl sulfate caused the ring opening to give corresponding 5. Also, treatment of 5 with phosphorus oxychloride gave 4-chloro-2-oxo-3-phenylthiazolidine-5-N-methylcarboxamide (6).