Dimethylformamide → 1-[3-(4-Fluoro-2-nitrophenoxy)propyl]-1,3,3-trimethylurea

HRID 2167455노트

반응식

HRID 2167455 반응식
[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

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 669172063-[3-(4-Fluoro-2-nitrophenoxy)propyl]-1,1-dimethyl urea

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f257b995bc154907a55f005bb0fa2717
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045464B2

반응 노트

불러오는 중…