Methyl iodide → HCID 19766727, compound

HRID 1196929Notes

Reaction equation

HRID 1196929 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11](=[O:19])[CH2:12][C:13]1[CH:18]=[N:17][CH:16]=[CH:15][N:14]=1.IC.[C:22](=O)(O)[O-].[Na+]>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)(Cl)Cl.ClCCl.C(O)(=O)C>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11](=[O:19])[CH:12]([C:13]1[CH:18]=[N:17][CH:16]=[CH:15][N:14]=1)[CH3:22]

Participants

10

Reactant 4

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 18956535HCID 18956535, compound

Product 1

HCID 19766727HCID 19766727, compound

Reagents, catalysts & solvents 5

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of sodium hydroxide (1.98 g) in water (40 ml) was added dropwise to a stirred, ice-cooled solution of the product of part (i) (5.80 g), iodomethane (8.79 g) and tetra-n-butylammonium hydrogen sulphate (8.40 g) in chloroform (40 ml). The mixture was stirred vigorously at room temperature for 3 hours and then diluted with water and dichloromethane. Acetic acid (3 ml) was added and the pH of the aqueous layer was adjusted to 7 with sodium bicarbonate. The organic layer was separated, washed twice with water and dried (Na2SO4). Evaporation of the solvent gave the crude product as an oil (5.57 g) which was used without further purification (the presence of 10% of the starting material [the product of part (i)] was indicated by N.M.R. spectroscopy).

Workup

  1. customThe organic layer was separated
  2. washwashed twice with water
  3. dry with materialdried (Na2SO4)
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-08119bdf977a498bbca10554b9dda084
Source dataset
uspto-grants-1992_05
Patent number
US05116844

Reaction notes

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