邻溴苯甲酸 → 2-bromo-N-(4-nitrophenyl)benzamide

HRID 5676

反应方程式

HRID 5676 反应方程式
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O.[N+:15]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)([O-:17])=[O:16]>C1(C)C=CC=CC=1.CN(C)C=O.CN1C(=O)CCC1>[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH:22][C:21]1[CH:23]=[CH:24][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=1)=[O:10]

参与物

7

反应物 3

HCID 6940邻溴苯甲酸HCID 74754-硝基苯胺HCID 24386氯化亚砜

产物 1

HCID 52125552-bromo-N-(4-nitrophenyl)benzamide收率 87%

试剂、催化剂与溶剂 3

HCID 1140甲苯溶剂2 次HCID 6228N,N-二甲基甲酰胺溶剂HCID 13387N-甲基吡咯烷酮溶剂

反应条件

温度
80 °C

实验过程

Thionyl chloride (120.5 g) was added to a stirred mixture of 2-bromobenzoic acid (194 g) in toluene (500 ml) and N,N-dimethylformamide (DMF) (5 ml) and the mixture heated at 80° C. for 4 hours. The solution was cooled to 20° C. and added slowly to a solution of 4-nitroaniline (133.1 g) in toluene (500 ml) and NMP (120 ml), maintaining the temperature of the reaction mixture between 20°-25° C. The reaction mixture was then stirred for 24 hours when a solid precipitated. Water (360 ml) was added with rigorous stirring and the suspended solid collected by filtration, and washed successively with water, toluene and acetonitrile to give 2-bromo-N-(4-nitrophenyl)benzamide as a solid, in 87% yield, which was used without further purification or characterisation.

后处理

  1. temperatureThe solution was cooled to 20° C.
  2. temperaturemaintaining the temperature of the reaction mixture between 20°-25° C
  3. customprecipitated
  4. additionWater (360 ml) was added
  5. stirringwith rigorous stirring
  6. filtrationthe suspended solid collected by filtration
  7. washwashed successively with water, toluene and acetonitrile

来源与证据

ORD记录
ord-55c8dbdb7e544eb9a79fb8565a5af017
来源数据集
uspto-grants-1993_09
专利号
US05245035

关联笔记

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