Methyl iodide → HCID 19773089, compound

HRID 1614231Notes

Reaction equation

HRID 1614231 reaction equation
[OH-].[K+].[OH:3][C:4]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)([C:7]1[CH:8]=[N:9][CH:10]=[C:11]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[CH:12]=1)[CH2:5][CH3:6].[CH3:30]I>CS(C)=O>[CH3:30][O:3][C:4]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)([C:7]1[CH:8]=[N:9][CH:10]=[C:11]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[CH:12]=1)[CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 19773095HCID 19773095, compound

Product 1

HCID 19773089HCID 19773089, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Powdered potassium hydroxide (0.155 g) was added to a solution of 2-[1-hydroxy-1-[5-(naphth-2-ylmethoxy)pyrid-3-yl]propyl]thiazole (0.218 g) in dimethylsulphoxide (2 ml) and the mixture was stirred at ambient temperature for 5 minutes. Methyl iodide (0.073 ml) was added and the mixture was stirred at ambient temperature for 30 minutes. The mixture was partitioned between water and methylene chloride (3×20 ml). The organic extracts were combined, dried (Na2SO4) and evaporated. The residue was purified by column chromatography eluting with increasingly polar mixtures of petrol (b.p. 60°-80° C.) and ethyl acetate to give 2-[1-methoxy-1-[5-(naphth-2-ylmethoxy)pyrid-3-yl]propyl]thiazole (0.14 g, 62%), m.p. 93°-95° C.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 30 minutes
  2. customThe mixture was partitioned between water and methylene chloride (3×20 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. washeluting
  7. temperaturewith increasingly polar mixtures of petrol (b.p. 60°-80° C.) and ethyl acetate

Sources & evidence

ORD record
ord-922ed7d71bde4ea4837af447ab340f04
Source dataset
uspto-grants-1993_03
Patent number
US05196422

Reaction notes

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