Methyl iodide → HCID 19817746, compound

HRID 1087181Notes

Reaction equation

HRID 1087181 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[CH:13]=[C:14]([C:21]2([CH3:26])[O:25][CH2:24][CH2:23][O:22]2)[CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19].[CH3:27]I>CN(C)C=O>[CH3:27][N:11]([C:12]1[CH:13]=[C:14]([C:21]2([CH3:26])[O:22][CH2:23][CH2:24][O:25]2)[CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:5]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:4]=1[F:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 103149282-[3-(2,4-Difluorophenylamino)-4-nitrophenyl]-2-methyl-1,3-dioxolane

Product 1

HCID 19817746HCID 19817746, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60%; 0.14 g) was added portionwise to an ice-cooled solution of 2-[3-(2,4-difluorophenylamino)-4-nitrophenyl]-2-methyl-1,3-dioxolane (1 g) in N,N-dimethylformamide. To the resulting mixture as added methyl iodide (1.7 g). The mixture was stirred at 0° C. for 30 minutes, poured into ice-water (50 ml) and extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The oily residue was purified by column chromatography on silica gel (30 g) eluting with toluene to give an oil of 2-{3-[N-methyl-N-(2,4-difluorophenyl)amino]-4-nitrophenyl}-2-methyl-1,3-dioxolane (0.88 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customevaporated
  5. customThe oily residue was purified by column chromatography on silica gel (30 g)
  6. washeluting with toluene

Sources & evidence

ORD record
ord-ad068f835b634fec9e7e354cc6fb894d
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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