N-(Ethoxycarbonyl)-4-chlorobenzenethiocarboxamide | 57774-74-0

• 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: N-(Ethoxycarbonyl)-4-chlorobenzenethiocarboxamide
• 英文别名: N-Ethoxycarbonyl-4-chlorphenyl-thioamid；N-carboethoxy-4-chlorobenzene thioamide；Carbamic acid, [(4-chlorophenyl)thioxomethyl]-, ethyl ester；ethyl N-(4-chlorobenzenecarbothioyl)carbamate
• CAS: 57774-74-0
• 化学式: C₁₀H₁₀ClNO₂S
• 分子量: 243.714
• InChiKey: DRZMNTBLMDGJGN-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(Ethoxycarbonyl)-4-chlorobenzenethiocarboxamide 以51%的产率得到
  参考文献：
  名称：

  GEORGE B.; PAPADOPOULOS E. P., J. ORG. CHEM., 1976, 41, NO 20, 3233-3237

  摘要：

  DOI：
• 作为产物：
  描述：

  三丁基(4-氯苯基)锡烷 、 异硫氰酰甲酸乙酯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到N-(Ethoxycarbonyl)-4-chlorobenzenethiocarboxamide
  参考文献：
  名称：

  Tin for organic synthesis. 10. Unconventional regiospecific syntheses of aromatic carbonamides and thiocarbonamides by means of tin-mediated Friedel-Crafts reactions

  摘要：

  Friedel-Crafts reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N-tosylcarbonamides 3 via ipso substitution of the stannyl group. Thus, unconventionally substituted aromatic carbonamides can be obtained. The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N-(arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on both aromatic rings. The known ipso-specific substitutions of stannylarenes with 14 are extended to bi- and tricyclic arenes as well as to thiophenes 6 and 22. One stannyl group can serve as a leaving group for two aromatic systems, as shown with diaryldialkyltins 29. Also, stannylalkanes such as 27 react with 14 to afford alkylsulfonyl isocyanates and products of further reactions, such as 28. From the reactions of 1 with ethoxycarbonyl isothiocyanate (32), ortho- and meta-substituted aromatic thiocarbonamides 33 which are potential precursors for further syntheses, are accessible. The scope, limitations, and mechanism of these electrophilic substitutions are outlined.

  DOI：

  10.1021/jo00077a020

文献信息

• Synthesis and Characterization of Some Novel Complexes of Rh(I), Pd(0) and Pt(0) with N-Carboethoxy-4-chlorobenzene and N-Carboethoxy-4-bromobenzene Thioamide Ligands
  作者：Sunil K. Misra、Umesh C. Tewari

  DOI：10.1080/15533170802525985

  日期：2008.12.10

  Reactions of ligands N-Carboethoxy-4-chlorobenzene thio amide (Hcct) and N-Carboethoxy-4-bromobenzene thioamide (Hcbt) with [Rh1Cl-(PPh3)3]. [Pd0(PPh3)4], [Pt0(PPh3)4] yields [Rh1Cl(HL)2(PPhf3)], [Pd0(HL)2(PPh3)2], [Pt0(HL)2(PPh3)2], respectively. The coordination modes of the ligands have been established on the basis of analytical, IR, electronic, spectral and magnetic measurements.
• Heterocycles from N-ethoxycarbonylthioamides and dinucleophilic reagents. 1. Dihydro-1,2,4-triazolones and 1,2,4-oxadiazolones
  作者：Babu George、Eleftherios P. Papadopoulos

  DOI：10.1021/jo00882a003

  日期：1976.10
• SYNTHESIS AND CHARACTERIZATION OF COPPER(I) COMPLEXES OF N-CARBOETHOXY-4-CHLOROBENZENE AND N-CARBOETHOXY-4-BROMOBENZENE THIOAMIDES (Hcct AND Hcbt)
  作者：Sunil K. Misra、U. C. Tewari

  DOI：10.1081/sim-120016465

  日期：2002.1.12

  Reactions of [Cu(EPh3)(3)X] with the title ligands yield [Cu(EPh3)(2)(LH)X] (LH = Hcct and Hcbt). Twelve complexes have been prepared and characterized on the basis of analytical, IR, electronic and NMR spectral and magnetic measurements. These complexes have a tetrahedral structure with the aromatic ligand bonded to copper(l) through sulfur.
• PAPADOPULOS E. P., J. ORG. CHEM. <JOCE-AH>, 1976, 41, NO 6, 962-965
  作者：PAPADOPULOS E. P.

  DOI：——

  日期：——
• Tin for organic synthesis. 10. Unconventional regiospecific syntheses of aromatic carbonamides and thiocarbonamides by means of tin-mediated Friedel-Crafts reactions
  作者：Martin Arnswald、Wilhelm P. Neumann

  DOI：10.1021/jo00077a020

  日期：1993.12

  Friedel-Crafts reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N-tosylcarbonamides 3 via ipso substitution of the stannyl group. Thus, unconventionally substituted aromatic carbonamides can be obtained. The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N-(arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on both aromatic rings. The known ipso-specific substitutions of stannylarenes with 14 are extended to bi- and tricyclic arenes as well as to thiophenes 6 and 22. One stannyl group can serve as a leaving group for two aromatic systems, as shown with diaryldialkyltins 29. Also, stannylalkanes such as 27 react with 14 to afford alkylsulfonyl isocyanates and products of further reactions, such as 28. From the reactions of 1 with ethoxycarbonyl isothiocyanate (32), ortho- and meta-substituted aromatic thiocarbonamides 33 which are potential precursors for further syntheses, are accessible. The scope, limitations, and mechanism of these electrophilic substitutions are outlined.