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

HRID 1477122Notes

Reaction equation

HRID 1477122 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-6e6acb1763c74b2789b6d222f197cff2
Source dataset
uspto-grants-2016_08
Patent number
US09403773B2

Reaction notes

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