异丙醇 → 2-fluoro-4-isopropyl-N-methoxycarbonylaniline

HRID 2116812

反应方程式

HRID 2116812 反应方程式
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[NH:4][C:5]([O:7][CH3:8])=[O:6].[CH:13](O)([CH3:15])[CH3:14].CCCCCC>S(=O)(=O)(O)O>[F:1][C:2]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:10]=[CH:9][C:3]=1[NH:4][C:5]([O:7][CH3:8])=[O:6]

参与物

5

反应物 3

HCID 3776异丙醇HCID 8058正己烷HCID 34841742-fluoro-N-methoxycarbonylaniline

产物 1

HCID 102625682-fluoro-4-isopropyl-N-methoxycarbonylaniline收率 53.3%

试剂、催化剂与溶剂 1

HCID 1118四氧化硫溶剂

反应条件

温度
70 °C

实验过程

2-Fluoro-N-methoxycarbonylaniline (1.00 g, 5.92 mmol) prepared as described in Example 1 was dissolved in 77.6% sulfuric acid (5.00 g) to prepare a solution. Isopropyl alcohol (0.400 g, 6.51 mmol) was added to the solution under a nitrogen atmosphere while stirring and heating the solution at 70° C. The mixture was vigorously stirred for 3 hr. The reaction solution was cooled to room temperature. n-Hexane (10 mL) was then added to the cooled reaction solution to carry out extraction for separation of the mixture into a sulfuric acid layer and an organic layer, and this extraction was carried out once again. The organic layers thus obtained were combined, and the combined organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine in that order. The solvent was then removed from the organic layer by distillation to give 666 mg of 2-fluoro-4-isopropyl-N-methoxycarbonylaniline as an oil. The oil was further subjected to separation and purification by column chromatography on silica gel to give 206 mg of 2-fluoro-4-isopropyl-N-methoxycarbonylaniline (yield 17.0%).

后处理

  1. customto prepare a solution
  2. stirringThe mixture was vigorously stirred for 3 hr
  3. temperatureThe reaction solution was cooled to room temperature
  4. extractionextraction
  5. customfor separation of the mixture into a sulfuric acid layer
  6. extractionan organic layer, and this extraction
  7. customThe organic layers thus obtained
  8. washthe combined organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine in that order
  9. customThe solvent was then removed from the organic layer by distillation

来源与证据

ORD记录
ord-aedcec1454ba4c1ea98d44db15d56ad8
来源数据集
uspto-grants-2008_10
专利号
US07439382B2

关联笔记

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