4-bromo-2-hydrazino-6-methylbenzothiazole | 1188226-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 4-bromo-2-hydrazino-6-methylbenzothiazole
• 英文别名: 4-Bromo-2-hydrazinyl-6-methylbenzothiazole；(4-bromo-6-methyl-1,3-benzothiazol-2-yl)hydrazine
• CAS: 1188226-87-0
• 化学式: C₈H₈BrN₃S
• 分子量: 258.142
• InChiKey: LWJAYFFZONSBSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  407.9±55.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-bromo-2-hydrazino-6-methylbenzothiazole 、 尿素 反应 3.0h， 以46.4%的产率得到5-bromo-3-hydroxy-7-methyl-1,2,4-triazolo-[3,4-b]-benzothiazole
  参考文献：
  名称：

  Novel Synthesis and Antimicrobial Activity of 3-Substituted 5-bromo-7-methyl-1,2,4-triazolo-[3,4-b]-benzothiazoles

  摘要：

  4‐Methyl acetanilide (1) on treatment with bromine in acetic acid, followed by hydrolysis with dilute HCl/NaOH solution, yielded 2‐bromo‐4‐methyl aniline (2), which on treatment with sodium thiocyanate in acetic acid afforded 2‐amino‐4‐bromo‐6‐methyl benzothiazole (3). Compound 3 in ethylene glycol was heated at 150°C with 80% hydrazine hydrate to get 4‐bromo‐2‐hydrazino‐6‐methyl benzothiazole (4). This hydrazino compound 4 on heating with formic acid for 3 h yielded 4‐bromo‐2‐hydrazinoformyl‐6‐methyl benzothiazole (5). Same compound 4 when heated independently with formic acid for 6 h/urea for 3 h/carbon disulfide in alkali afforded 5‐bromo‐7‐methyl (6)/5‐bromo‐3‐hydroxy‐7‐methyl (7)/5‐bromo‐3‐mercapto‐7‐methyl (8)‐1,2,4‐triazolo‐[3,4‐b]‐benzothiazoles, respectively. Compound 4 on heating with acetic acid/acetic anhydride gave acetyl benzothiazolyl derivative 9, which on cyclization with orthophosphoric acid yielded 5‐bromo‐3,7‐dimethyl‐1,2,4‐triazolo‐[3,4‐b]‐benzothiazole (10). All these newly synthesized compounds were screened for antimicrobial activity against Escherichia coli (Gram −ve), Bacillus subtilis (Gram +ve), Erwinia carotovora, and Xanthomonas citri using ampicillin, streptomycin, and penicillin as a standard for comparison.

  DOI：

  10.1002/jhet.885
• 作为产物：
  描述：

  4-甲基乙酰苯胺 在 盐酸 、 溴 、 一水合肼 、 sodium hydroxide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 4-bromo-2-hydrazino-6-methylbenzothiazole
  参考文献：
  名称：

  Novel Synthesis and Antimicrobial Activity of 3-Substituted 5-bromo-7-methyl-1,2,4-triazolo-[3,4-b]-benzothiazoles

  摘要：

  4‐Methyl acetanilide (1) on treatment with bromine in acetic acid, followed by hydrolysis with dilute HCl/NaOH solution, yielded 2‐bromo‐4‐methyl aniline (2), which on treatment with sodium thiocyanate in acetic acid afforded 2‐amino‐4‐bromo‐6‐methyl benzothiazole (3). Compound 3 in ethylene glycol was heated at 150°C with 80% hydrazine hydrate to get 4‐bromo‐2‐hydrazino‐6‐methyl benzothiazole (4). This hydrazino compound 4 on heating with formic acid for 3 h yielded 4‐bromo‐2‐hydrazinoformyl‐6‐methyl benzothiazole (5). Same compound 4 when heated independently with formic acid for 6 h/urea for 3 h/carbon disulfide in alkali afforded 5‐bromo‐7‐methyl (6)/5‐bromo‐3‐hydroxy‐7‐methyl (7)/5‐bromo‐3‐mercapto‐7‐methyl (8)‐1,2,4‐triazolo‐[3,4‐b]‐benzothiazoles, respectively. Compound 4 on heating with acetic acid/acetic anhydride gave acetyl benzothiazolyl derivative 9, which on cyclization with orthophosphoric acid yielded 5‐bromo‐3,7‐dimethyl‐1,2,4‐triazolo‐[3,4‐b]‐benzothiazole (10). All these newly synthesized compounds were screened for antimicrobial activity against Escherichia coli (Gram −ve), Bacillus subtilis (Gram +ve), Erwinia carotovora, and Xanthomonas citri using ampicillin, streptomycin, and penicillin as a standard for comparison.

  DOI：

  10.1002/jhet.885

文献信息

• Novel Synthesis and Antimicrobial Activity of 3-Substituted 5-bromo-7-methyl-1,2,4-triazolo-[3,4-<i>b</i>]-benzothiazoles
  作者：T. M. Bhagat、S. K. Deshmukh、S. V. Kuberkar

  DOI：10.1002/jhet.885

  日期：2012.7

  4‐Methyl acetanilide (1) on treatment with bromine in acetic acid, followed by hydrolysis with dilute HCl/NaOH solution, yielded 2‐bromo‐4‐methyl aniline (2), which on treatment with sodium thiocyanate in acetic acid afforded 2‐amino‐4‐bromo‐6‐methyl benzothiazole (3). Compound 3 in ethylene glycol was heated at 150°C with 80% hydrazine hydrate to get 4‐bromo‐2‐hydrazino‐6‐methyl benzothiazole (4). This hydrazino compound 4 on heating with formic acid for 3 h yielded 4‐bromo‐2‐hydrazinoformyl‐6‐methyl benzothiazole (5). Same compound 4 when heated independently with formic acid for 6 h/urea for 3 h/carbon disulfide in alkali afforded 5‐bromo‐7‐methyl (6)/5‐bromo‐3‐hydroxy‐7‐methyl (7)/5‐bromo‐3‐mercapto‐7‐methyl (8)‐1,2,4‐triazolo‐[3,4‐b]‐benzothiazoles, respectively. Compound 4 on heating with acetic acid/acetic anhydride gave acetyl benzothiazolyl derivative 9, which on cyclization with orthophosphoric acid yielded 5‐bromo‐3,7‐dimethyl‐1,2,4‐triazolo‐[3,4‐b]‐benzothiazole (10). All these newly synthesized compounds were screened for antimicrobial activity against Escherichia coli (Gram −ve), Bacillus subtilis (Gram +ve), Erwinia carotovora, and Xanthomonas citri using ampicillin, streptomycin, and penicillin as a standard for comparison.