Methyl iodide → HCID 11741253, compound

HRID 1587406Notes

Reaction equation

HRID 1587406 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[CH3:28]I>C(Cl)(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]([C:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH:23]=3)[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 10248841HCID 10248841, compound

Product 1

HCID 11741253HCID 11741253, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 4,5-bis(4-methoxyphenyl)-2-(4-pyridyl)thiazole (1.78 g) and methyl iodide (2.96 ml) in a mixture of chloroform and methanol (5:2) (28 ml) was allowed to stand at ambient temperature for 2 days. The reaction mixture was evaporated in vacuo and the residue containing 4-[4,5-bis(4-methoxyphenyl)thiazol-2-yl]-1-methylpyridinium iodide was dissolved in a mixture of methanol (20 ml). To the resulting solution was added portionwise sodium borohydride (0.54 g) with stirring at 5° to 10° C. The reaction mixture was stirred for one hour at the same temperature. Water was added to the reaction mixture and the precipitate was collected by filtration. The precipitate was dissolved in chloroform and washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was recrystallized from a aqueous methanol to give 4,5-bis(4-methoxyphenyl)-2-(1-methyl-1,2,5,6-tetrahydro-4-pyridyl)thiazole (0.16 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionthe residue containing 4-[4,5-bis(4-methoxyphenyl)thiazol-2-yl]-1-methylpyridinium iodide
  3. dissolutionwas dissolved in a mixture of methanol (20 ml)
  4. additionTo the resulting solution was added portionwise sodium borohydride (0.54 g)
  5. stirringThe reaction mixture was stirred for one hour at the same temperature
  6. additionWater was added to the reaction mixture
  7. filtrationthe precipitate was collected by filtration
  8. dissolutionThe precipitate was dissolved in chloroform
  9. washwashed with brine
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent was evaporated in vacuo
  12. customthe residue was recrystallized from a aqueous methanol

Sources & evidence

ORD record
ord-7e7a94bbeebd41daafa1e82d2819c796
Source dataset
uspto-grants-1993_06
Patent number
US05217971

Reaction notes

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