Methyl iodide → HCID 22003666, compound

HRID 324438Notes

Reaction equation

HRID 324438 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][C:5]2[CH:6]([C:15]3[C:16](=[O:22])[NH:17][C:18](=[O:21])[NH:19][CH:20]=3)[C:7]3[C:8]([CH:13]=[CH:14][C:4]=2[CH:3]=1)=[N:9][CH:10]=[CH:11][CH:12]=3.[H-].[Na+].I[CH3:28]>CN(C)C=O.O>[CH3:28][N:19]1[CH:20]=[C:15]([CH:6]2[C:7]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[CH:13]=[CH:14][C:4]3[CH:3]=[C:2]([CH3:1])[CH:24]=[CH:23][C:5]2=3)[C:16](=[O:22])[NH:17][C:18]1=[O:21]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22003606HCID 22003606, compound

Product 1

HCID 22003666HCID 22003666, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of the product of example 22 step (iv) (0.68 g) in dry N,N-dimethylformamide (10 ml) was treated in one portion with sodium hydride (60% dispersion by wt, 0.086 g). After 1 hr iodomethane (0.13 ml) was added and the solution was stirred for 16 hr. The reaction mixture was diluted with water (50 ml) and the mixture was extracted with ethyl acetate (3×20 ml). The combined extracts were dried (Na2SO4) and the solvent was evaporated under reduced pressure. Purification was by chromatography eluting with 50-60% acetone in isohexane.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×20 ml)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customthe solvent was evaporated under reduced pressure
  4. customPurification
  5. washeluting with 50-60% acetone in isohexane

Sources & evidence

ORD record
ord-cfd3ab6505e1474c86a8c866d4566e5a
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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