硝基氯苯 → N-(4-chloro-3-nitrobenzyl)-2,2,2-trifluoroacetamide

HRID 59289

反应方程式

HRID 59289 反应方程式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].O[CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

参与物

4

反应物 2

HCID 6945硝基氯苯HCID 3084931N-(羟甲基)三氟乙酰胺

产物 1

HCID 19879857N-(4-chloro-3-nitrobenzyl)-2,2,2-trifluoroacetamide收率 30,891.9%

试剂、催化剂与溶剂 1

HCID 1118四氧化硫溶剂

反应条件

温度
75 °C

实验过程

To a solution of 1-chloro-2-nitrobenzene (10.0 g, 0.063 mmol) in conc. sulphuric acid (150 mL) was added N-hydroxy methyl trifluoro acetamide (9.98 g, 0.069 mmol). The reaction mixture was heated at 70-80° C. for 24 h. The reaction mass was quenched in ice cold water, neutralised with sodium hydroxide and extracted with DCM. The organic layer was concentrated and the obtained crude product was purified by column chromatography on silica gel eluting with 4% EtOAc: pet. ether to afford 5.5 g of desired product. 1H NMR (300 MHz, DMSO d6): 4.48 (d, J=3.9 Hz, 2H), 7.62-7.64 (m, 1H), 7.72-7.78 (m, 1H), 7.97-8.01 (m, 1H), 10.09 (brs, 1H).

后处理

  1. customThe reaction mass was quenched in ice cold water
  2. extractionextracted with DCM
  3. concentrationThe organic layer was concentrated
  4. customthe obtained crude product
  5. customwas purified by column chromatography on silica gel eluting with 4% EtOAc

来源与证据

ORD记录
ord-d0adaacf7d1f472794d4e88810d0c6df
来源数据集
uspto-grants-2016_09
专利号
US09439890B2

关联笔记

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