Potassium Iodide → 1-(2-ethoxyethyl)-1H-imidazole-2-carbaldehyde

HRID 77601

Reaction equation

HRID 77601 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].Br[CH2:9][CH2:10][O:11][CH2:12][CH3:13].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH2:10]([O:11][CH2:12][CH2:13][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7])[CH3:9]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 249551H-imidazole-2-carbaldehydeHCID 611412-Bromoethyl ethyl ether

Product 1

HCID 594087081-(2-ethoxyethyl)-1H-imidazole-2-carbaldehydeYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of imidazole-2-carboxaldehyde (2.00 g, 21 mmol) in DMF (1 mL) was added 1.1 eq. of 1-bromo-2-ethoxyethane (3.51 g, 22 mmol), potassium carbonate and a catalytic amount of potassium iodide. The reactions were heated at 110° C. for 18 hrs followed by evaporation to dryness and purified utilizing a Biotage SP4 with a gradient method of 5-50% methanol in DCM to yield the desired compound (580 mg, 3.56 mmol, 17% yield). 1H NMR (400 MHz, DMSO-d6) δ 9.63 (s, H), 7.6 (s, H), 7.21 (s, H), 4.45 (dd, 2H), 3.62 (dd, 2H), 3.38 (m, 2H), 1.05 (t, 3H).

Workup

  1. customfollowed by evaporation to dryness
  2. custompurified

Sources & evidence

ORD record
ord-cf435f512b2f4463971637ac5ed95ded
Source dataset
uspto-grants-2014_09
Patent number
US08840865B2

Linked notes

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