Carbonochloridimidothioic acid, (2,6-dimethylphenyl)-, methyl ester | 94518-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Carbonochloridimidothioic acid, (2,6-dimethylphenyl)-, methyl ester
• 英文别名: N-(2,6-dimethylphenyl)-1-methylsulfanylmethanimidoyl chloride
• CAS: 94518-64-6
• 化学式: C₁₀H₁₂ClNS
• 分子量: 213.731
• InChiKey: FKIRSQCVCMQMSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Carbonochloridimidothioic acid, (2,6-dimethylphenyl)-, methyl ester 在 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.0h， 生成 5-(tert-butylimino)-1-(2,6-dimethylphenyl)-4,4-diphenyl-2-(methylthio)-2-imidazoline
  参考文献：
  名称：

  Reactions of protonated 1,3-diaza,-4,4-diphenyl-2-(methylthio)butadienes with isocyanides: preparation of imidazole and triazine derivatives

  摘要：

  DOI：

  10.1021/jo00266a035
• 作为产物：
  描述：

  氯硫基甲烷 、 2,6-二甲基苯基异腈 以 四氢呋喃 为溶剂， 生成 Carbonochloridimidothioic acid, (2,6-dimethylphenyl)-, methyl ester
  参考文献：
  名称：

  Three-component cyclocondensations. Two methods for the efficient preparation of 5-aminothiazolium salts via the reaction of isocyanides either with dimethylthioformamide and imino chloro sulfides or benzaldimines and aryl chlorothioformates

  摘要：

  Treatment of imino chloro sulfides with dimethylthioformamide and isocyanides at room temperature provides selectively the 5-amino-4-(dimethylamino)-2-(methylthio)(or phenylthio)thiazolium salts. Similarly, the reactions of p-tolyl chlorothionoformate and phenyl chlorodithioformate with a mixture of benzaldimine and isocyanide afford rapidly the 5-amino-4-phenylthiazolium salts. We suggest that these reactions involve the N-(thiocarbonyl)formamidinium and benzylideniminium chlorides as transient intermediates, which are trapped by isocyanides according to a [1 + 4] cycloaddition process. The structure of the thiazolium salts and some of their reactivities are discussed.

  DOI：

  10.1021/jo00074a032

文献信息

• Three-component cyclocondensations. A convenient access to fused imidazolium and dihydropyrimidinium salts via the reaction of methyl chlorothioimidates with azines and isocyanides.
  作者：Evelyne Marchand、Georges Morel

  DOI：10.1016/s0040-4039(00)77603-9

  日期：1993.4

  and pyrinidine react in a sequence of N-imidoylpyridinium formation then cycloaddition step, to give 1-amonoimidazo [1,5-a] pyridazine, pyrimidine and pyrazine allows the preparation of corresponding fused 1 -amino-3-(methylthio) imidazolium chlorides.

  氯硫代亚氨酸甲酯，异氰酸酯和嘧啶的混合物按N-亚氨基吡啶鎓的形成顺序反应，然后环加成步骤，得到1-单咪唑并[1,5-a]哒嗪，嘧啶和吡嗪，可以制备相应的稠合1-氨基-3 -（甲硫基）咪唑鎓氯化物。
• New imidoyl isothiocyanates. Chemical behavior in polar solvents. Reaction with sulfenyl thiocyanates: preparation of 1,2-dihydro-2-thioxo-1,3,5-triazines and 1,3,4,6,6a-triazadithia[6aS(IV)]pentalenes
  作者：Georges Morel、Evelyne Marchand、Catherine Haquin、Andre Foucaud

  DOI：10.1021/jo00371a024

  日期：1986.10
• Three-component cyclocondensations. An efficient synthesis of 4-amino-2-(methylthio)imidazolium salts via the reaction of methyl chlorothioimidates with benzaldimines and isocyanides. Autoxidation of the imidazole derivatives
  作者：Yvelise Malvaut、Evelyne Marchand、Georges Morel

  DOI：10.1021/jo00033a038

  日期：1992.3

  Treatment of imino chlorosulfides 1 with a mixture of benzaldimine and isocyanide provides 4-aminoimidazolium chlorides 5. Presumably this reaction involves the N-imidoylbenzylideniminium chlorides 4 as transient intermediates. 1- and 3-tert-Butyl imidazolium salts 5 undergo fast isobutene elimination giving the corresponding imidazole and imidazoline hydrochlorides 10 and 13. Compounds 13 autoxidize to afford 5-hydroxy derivatives 14 under atmospheric oxygen. The structural assignment of 14 has been confirmed by X-ray diffraction analysis. Under similar conditions, treatment of ketimines 17 with methyl chlorothioimidate 1 and isocyanide gives 2-thioxodiazolidines 19.
• C-(Methoxycarbonyl)ketene N-imidoylimine synthesis and rearrangement into methyl 4,6-diazahepta-2,4,6-trienoates. Cycloaddition reactions with isocyanides: preparation of imidazolines
  作者：Georges Morel、Evelyne Marchand、Andre Foucaud

  DOI：10.1021/jo00206a009

  日期：1985.3
• Three-component cyclocondensations. Two methods for the efficient preparation of 5-aminothiazolium salts via the reaction of isocyanides either with dimethylthioformamide and imino chloro sulfides or benzaldimines and aryl chlorothioformates
  作者：Fabienne Berree、Yvelise Malvaut、Evelyne Marchand、Georges Morel

  DOI：10.1021/jo00074a032

  日期：1993.10

  Treatment of imino chloro sulfides with dimethylthioformamide and isocyanides at room temperature provides selectively the 5-amino-4-(dimethylamino)-2-(methylthio)(or phenylthio)thiazolium salts. Similarly, the reactions of p-tolyl chlorothionoformate and phenyl chlorodithioformate with a mixture of benzaldimine and isocyanide afford rapidly the 5-amino-4-phenylthiazolium salts. We suggest that these reactions involve the N-(thiocarbonyl)formamidinium and benzylideniminium chlorides as transient intermediates, which are trapped by isocyanides according to a [1 + 4] cycloaddition process. The structure of the thiazolium salts and some of their reactivities are discussed.