Methyl iodide → HCID 178487499, compound

HRID 1368528Notes

Reaction equation

HRID 1368528 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([CH:15]([C:17]1[N:18]=[CH:19][N:20](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:21]=1)[OH:16])[CH:9]=[CH:8]2.[H][H].[CH3:43]I>O.CN(C=O)C.C1COCC1>[CH3:43][O:16][CH:15]([C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[CH:13][CH:14]=[C:5]([O:4][CH3:3])[CH:6]=2)[CH:11]=1)[C:17]1[N:18]=[CH:19][NH:20][CH:21]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11092260(6-methoxynaphthalen-2-yl)-(1-trityl-1H-imidazol-4-yl)methanolHCID 178418361HCID 178418361, compound

Product 1

HCID 178487499HCID 178487499, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% oil dispersion, 1.77 g) was added to a mixture of THF (200 ml) and DMF(100 ml). To the mixture was added (6-methoxynaphthalen-2-yl)-(1-trityl-1H-imidazol-4-yl)methanol (20.0 g). The mixture was heated at 50 until the evolution of hydrogen ceased. The mixture was cooled to 0° C., and to the mixture was added methyl iodide (2.6 ml). The mixture was stirred for 15 min. Water was added to the reaction mixture to quench the reaction. THF was distilled off under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated aqueous solution of sodium chloride, dried and concentrated. The residue was recrystallized from ethyl acetate-hexane to give the titled compound (18.6 g) as a colorless powder.

Workup

  1. customto quench
  2. customthe reaction
  3. distillationTHF was distilled off under reduced pressure
  4. additionTo the residue was added water
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water and saturated aqueous solution of sodium chloride
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b4a17a72d4d74a8b995f02b345570928
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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