Methyl iodide → HCID 19093551, compound

HRID 2372271Notes

Reaction equation

HRID 2372271 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[C:7]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[N:18])=[CH:6][C:5]=1[O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[N:25])(=[O:3])[CH3:2].[H-].[Na+].[CH3:28]I>CN(C)C=O>[C:1]([C:4]1[CH:9]=[C:8]([CH2:10][O:11][CH3:28])[C:7]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[N:18])=[CH:6][C:5]=1[O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[N:25])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14820151HCID 14820151, compound

Product 1

HCID 19093551HCID 19093551, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 688 mg of 5,5'-[(4-acetyl-6-hydroxymethyl-1,3-phenylene)bis(oxy)]bis pentanenitrile]in 15 ml of dimethylformamide was added to a suspension of 0.184 of a 50% oil dispersion of sodium hydride and 0.62 ml of methyl iodide in 45 ml of dimethylformamide at 0° C. The reaction was allowed to come to room temperature and stirred overnight. The reaction mixture was partitioned between ethyl acetate and dilute hydrochloric acid to which sodium chloride had been added. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. The resulting residue was purified by high pressure liquid chromatography over silica gel eluting with a 0-70% ethyl acetate in hexane gradient to provide 110 mg of the desired title product. NMR, MS.

Workup

  1. customto come to room temperature
  2. customThe reaction mixture was partitioned between ethyl acetate and dilute hydrochloric acid to which sodium chloride
  3. additionhad been added
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by high pressure liquid chromatography over silica gel eluting with a 0-70% ethyl acetate in hexane gradient

Sources & evidence

ORD record
ord-a8666666180648b9b02e547465aff6e1
Source dataset
uspto-grants-1992_03
Patent number
US05098613

Reaction notes

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