Chlorosuccinimide → ethyl 4-chloro-5-ethyl-1H-imidazole-2-carboxylate

HRID 43431Notes

Reaction equation

HRID 43431 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.[CH2:9]([C:11]1[NH:15][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][CH:12]=1)[CH3:10].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:8][C:12]1[N:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:15][C:11]=1[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 14990237Ethyl 5-ethyl-1H-imidazole-2-carboxylate

Product 1

HCID 67549841ethyl 4-chloro-5-ethyl-1H-imidazole-2-carboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

NCS (3.15 g, 23.59 mmol) was added to a solution of ethyl 5-ethyl-1H-imidazole-2-carboxylate obtained in Example (1b) (3.35 g, 19.92 mmol) in chloroform (100 mL), and the mixture was stirred at room temperature for 28 hours. Saturated aqueous sodium bicarbonate solution was added to the reaction solution, followed by extraction with chloroform. Then, the organic layer was washed with brine and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 3/1) to obtain 1.81 g of the title compound as a pale yellow solid (45%).

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThen, the organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentration under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 3/1)

Sources & evidence

ORD record
ord-b812c666a60842abbc8e481aea650a40
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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