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

HRID 2388105ノート

反応式

HRID 2388105 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-88218251068748ca92e064524a530eab
出典データセット
uspto-grants-2012_09
特許番号
US08269011B2

反応ノート

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