Imidazole → 2-(1-Imidazolylmethyl)naphtho[1,2-d]thiazole

HRID 865108Notes

Reaction equation

HRID 865108 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Br[CH2:9][C:10]1[S:11][C:12]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]=2[N:14]=1>O1CCCC1>[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH2:9][C:10]1[S:11][C:12]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 189410952-Bromomethylnaphtho[1,2-d]thiazole

Product 1

HCID 677715272-(1-Imidazolylmethyl)naphtho[1,2-d]thiazoleYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.06 g of sodium hydride (60%) was added to a solution of 0.10 g of imidazole in tetrahydrofuran (30 ml). After 30 minutes of stirring at room temperature, a solution of 2-bromomethylnaphtho[1,2-d]thiazole in tetrahydrofuran (10 ml) was added to the solution. After stirring at room temperature for 1 hour and evaporation of the solvent, the residue was partitioned between 1N hydrochloric acid and ethyl acetate. The organic layer was extracted with 1N hydrochloric acid. The combined aqueous layer was neutralized with sodium bicarbonate and then extracted with chloroform. After drying over anhydrous magnesium sulfate, the solvent was evaporated to obtain 0.27 g (100%) of 2-(1-imidazolylmethyl)naphtho[1,2-d]thiazole. This free base was dissolved in methanol and mixed with 0.10 g of fumaric acid to effect crystallization to give 0.32 g of fumarate.

Workup

  1. stirringAfter stirring at room temperature for 1 hour
  2. customevaporation of the solvent
  3. customthe residue was partitioned between 1N hydrochloric acid and ethyl acetate
  4. extractionThe organic layer was extracted with 1N hydrochloric acid
  5. extractionextracted with chloroform
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d2b59979e3774f9bae72504a35d84ec3
Source dataset
uspto-grants-1996_10
Patent number
US05565479

Reaction notes

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