Imidazole → HCID 67173176, compound

HRID 872619Notes

Reaction equation

HRID 872619 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Br[CH2:9][C:10]1[S:14][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:12][CH:11]=1>CN(C=O)C>[N:3]1([CH2:9][C:10]2[S:14][C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:12][CH:11]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 49757954Ethyl 5-(bromomethyl)-1,3-thiazole-2-carboxylate

Product 1

HCID 67173176HCID 67173176, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a cooled (0 C) suspension of sodium hydride (60% in oil, 82 mg, 2.05 mmol) in dry DMF (2 ml) was added imidazole (93 mg, 1.37 mmol) as a solution in dry DMF (0.5 ml). Mixture was stirred at RT 45 min, cooled to 0° C. followed by addition of ethyl 5-(bromomethyl)thiazole-2-carboxylate (342 mg, 1.37 mmol) dissolved in dry DMF (2 ml). After being stirred at RT for 20 h, the reaction mixture was evaporated and the residue was taken up in DCM and washed twice with saturated NaCl solution. Thus, 143 mg (44%) of the title compound was obtained. 1H-NMR (400 MHz; d6-DMSO): δ 1.32 (t, 3H), 4.37 (q, 2H), 5.39 (s, 2H), 6.91 (s, 1H), 7.20 (s, 1H), 7.75 (s, 1H), 7.93 (s, 1H).

Workup

  1. temperatureTo a cooled
  2. temperaturecooled to 0° C.
  3. stirringAfter being stirred at RT for 20 h
  4. customthe reaction mixture was evaporated
  5. washwashed twice with saturated NaCl solution

Sources & evidence

ORD record
ord-12a2e719432549208b060e46e4736628
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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