N,N-二甲基甲酰胺 → 1-[3-(4-Fluoro-2-nitrophenoxy)propyl]-1,3,3-trimethylurea

HRID 238317笔记

反应方程式

HRID 238317 反应方程式
[H-].[Na+].[CH3:3]N(C=O)C.[F:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:22])[N:19]([CH3:21])[CH3:20])=[C:11]([N+:25]([O-:27])=[O:26])[CH:10]=1.CI>C(OCC)(=O)C.O>[F:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:3])[C:18]([N:19]([CH3:21])[CH3:20])=[O:22])=[C:11]([N+:25]([O-:27])=[O:26])[CH:10]=1

参与物

7

反应物 4

HCID 6228N,N-二甲基甲酰胺HCID 6328碘甲烷HCID 24758氢化钠HCID 669172063-[3-(4-Fluoro-2-nitrophenoxy)propyl]-1,1-dimethyl urea

产物 1

HCID 669172431-[3-(4-Fluoro-2-nitrophenoxy)propyl]-1,3,3-trimethylurea收率 40%

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8857乙酸乙酯溶剂

实验过程

Sodium hydride (55% in oil) (396 mg, 9.1 mmol) was added, while being cooled with ice, to a DMF solution (9 ml) of 2.0 g of 3-[3-(4-fluoro-2-nitrophenoxy)propyl]-1,1-dimethyl urea (7.0 mmol) and the mixture was stirred at room temperature for 5 minutes. Methyl iodide (0.735 ml, 11.8 mmol) was added to the mixture and the resulting mixture was stirred at room temperature for 48 hours. Water was added to the reaction mixture and extraction with ethyl acetate was performed. After being washed with a saturated sodium chloride aqueous solution, the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=9:1→6:1). The purified product was concentrated under reduced pressure to thereby obtain 0.83 g of oily pale yellow 1-[3-(4-fluoro-2-nitrophenoxy)propyl]-1,3,3-trimethylurea (yield: 40%).

后处理

  1. stirringthe resulting mixture was stirred at room temperature for 48 hours
  2. washAfter being washed with a saturated sodium chloride aqueous solution
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (dichloromethane:ethyl acetate=9:1→6:1)
  5. concentrationThe purified product was concentrated under reduced pressure

来源与证据

ORD记录
ord-9a69ca7742aa4b408e8d8e5155a6dab6
来源数据集
uspto-grants-2014_02
专利号
US08642619B2

反应笔记

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