2-(phenylthio)benzamide | 31913-94-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(phenylthio)benzamide
• 英文别名: 2-Phenylsulfanylbenzamide
• CAS: 31913-94-7
• 化学式: C₁₃H₁₁NOS
• 分子量: 229.302
• InChiKey: CPTFVDLLWNPUGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  170-174 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  408.8±28.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(phenylthio)benzamide 在 sodium azide 、 磷酸 、 双氧水 、 phosphorus pentoxide 、 三乙胺 作用下， 以 氯仿 为溶剂， 生成 3-ethoxycarbonylimino-1-phenyl-3H-1λ⁴-benzo[d]isothiazole 1-oxide
  参考文献：
  名称：

  Stoss,P.; Satzinger,G., Chemische Berichte, 1975, vol. 108, p. 3855 - 3863

  摘要：

  DOI：
• 作为产物：
  描述：

  N-丙-2-烯基苯甲酰胺 在 仲丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.33h， 生成 2-(phenylthio)benzamide
  参考文献：
  名称：

  Heteroatom-directed metalation. Lithiation of N-propenylbenzamides and N-propenyl-o-toluamides. Novel routes to ortho-substituted primary benzamide derivatives and N-unsubstituted isoquinolin-1(2H)-ones

  摘要：

  Reaction of N-propenylbenzamides 4 and 9, obtained by LDA-induced isomerization of the corresponding N-allylbenzamides 1, 8, and 14, with 2 equiv of sec-butyllithium or tert-butyllithium at low temperature regiospecifically generates the highly reactive N,ortho-dilithiated species (e.g., 5 and 17). These dilithio species react avidly with a wide spectrum of electrophilic reagents, including alkyl halides, giving adducts which on hydrolysis with warm 50% aqueous acetic acid are converted into ortho-substituted primary benzamides in excellent yields. Ortho-lithiation of N-propenylbenzamides is thus formally equivalent to ortho-lithiation of primary benzamides themselves. The utility of this important, previously unknown, synthetic operation is enhanced by the well-known facility with which the primary amide moiety can be transformed into other useful functional groups, as exemplified by the synthesis of 2-methoxy-6-methylbenzoic acid (12) and 2-methoxy-6-methylbenzonitrile (13) from N-propenyl-2-methoxybenzamide (9), N-Propenyl-o-toluamide (7) undergoes regiospecific dilithiation on nitrogen and on the methyl group under conditions analogous to those used for the N-propenylbenzamides. These dilithio species react with DMF or "Weinreb type" amides to give condensation products which cyclize to N-propenylisoquinolin-1(2H)-ones under midly acidic conditions. Removal of the N-propenyl moiety under more strongly acidic conditions provides N-unsubstituted isoquinolin-1(2H)-ones with high overall efficiency. This process is exemplified by the synthesis of isoquinolin-1(2H)-one (23) and its 3-n-butyl congener 26 from N-propenyl-2-methylbenzamide (7).

  DOI：

  10.1021/jo00035a030

文献信息

• Photochemistry of hydroxamic acids
  作者：B.D. Hosangadi、P.N. Chhaya、M.M. Nimbalkar、N.R. Patel

  DOI：10.1016/s0040-4020(01)87717-6

  日期：1987.1

  Photochemical reactions of hydroxamic acids have been studied. The intermediacy of a RCONH radical is postulated, based on oxidations achieved with DCA under photochemical conditions.

  已经研究了异羟肟酸的光化学反应。根据在光化学条件下用DCA进行的氧化，推测RCONH自由基的中间体。
• [EN] PREPARATION METHOD FOR QUETIAPINE<br/>[FR] PROCEDE DE PREPARATION DE QUETIAPINE
  申请人：FERMION OY

  公开号：WO2005028459A1

  公开（公告）日：2005-03-31

  The present invention discloses a process for the preparation of quetiapine, which comprises the ring closure and deprotection of a compound of the formula (I), as well as novel intermediates in the process.

  本发明揭示了一种制备奎哌齐平的方法，包括对式(I)化合物进行环闭合和去保护，以及该方法中的新型中间体。
• 2-Phenylthiobenzylamine dervivatives and acid addition salts thereof
  申请人：SPOFA Spojené Podniky Pro Zdravotnickou Vyrobu

  公开号：EP0396827A1

  公开（公告）日：1990-11-14

  N,N-Dimethyl-2-(3-hydroxyphenylthio)benzylamine and its acid addition salts possess properties of highly selective inhibitors of 5-hydroxytryptamine re-uptake in mammalian brain structures and are expected to find therapeutic use as potent central antidepressants. This novel compound and its intermediate, the 3-methoxyphenylthio analog, are available by per se known preparative routes, especially by reduction of the corresponding amides with hydride agents, by Leuckart reaction of 2-arylthiobenzaldehydes with dimethylformamide and formic acid, or by demethylation of the respective methoxy compound by means of e.g. pyridine hydrochloride or hydrobromic acid.

  N,N-二甲基-2-(3-羟基苯硫基)苯乙胺及其酸盐加合物具有高度选择性地抑制哺乳动物脑结构中的5-羟色胺再摄取的特性，预计可作为有效的中枢抗抑郁剂用于治疗。这种新型化合物及其中间体，即3-甲氧基苯硫基类似物，可通过已知的制备路线制备，特别是通过用氢化剂还原相应的酰胺，通过Leuckart反应将2-芳基硫代苯甲醛与二甲基甲酰胺和甲酸反应，或通过使用吡啶盐酸盐或氢溴酸对相应的甲氧基化合物进行脱甲基化制备。
• Phenylthioaralkylamines
  申请人：Merck & Co., Inc.

  公开号：US04018830A1

  公开（公告）日：1977-04-19

  Phenylthioaralkylamines and 2-phenylthiobenzylamines are prepared by reaction of the corresponding phenylthiobenzoyl chloride or homologs thereof with ammonia or an amine to produce the corresponding phenylthiobenzamide or N-substituted or N,N-disubstituted derivative thereof followed by reduction with lithium aluminum hydride to produce the corresponding phenylthiobenzylamine or the N-substituted or N,N-disubstituted derivative thereof. The compounds are also prepared by reaction of the corresponding phenylthiobenzyl halide with ammonia or a selected amine. The compounds are active as antiarrhythmics.

  苯硫代芳基胺和2-苯硫代苄基胺的制备方法是通过将相应的苯硫代苯甲酰氯或其同系物与氨或胺反应，生成相应的苯硫代苯甲酰胺或其N-取代或N,N-二取代衍生物，随后用氢化铝锂还原制备相应的苯硫代苄基胺或其N-取代或N,N-二取代衍生物。这些化合物也可以通过将相应的苯硫代苄卤与氨或选定的胺反应来制备。这些化合物作为抗心律失常剂具有活性。
• Preparation method for quetiapine
  申请人：Hilden Leif

  公开号：US20070111986A1

  公开（公告）日：2007-05-17

  The present invention discloses a process for the preparation of quetiapine, which comprises the ring closure and deprotection of a compound of the formula (I), as well as novel intermediates in the process.

  本发明揭示了一种制备喹硫平的方法，该方法包括环闭合和去保护化合物(I)的步骤，以及该过程中的新型中间体。