Sodium Carbonate → Ethyl 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-5-methyl-1h-imidazole-4-carboxylate

HRID 532240Notes

Reaction equation

HRID 532240 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[NH:18])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[CH:4][CH:3]=1.Br[CH:20]([CH3:28])[C:21](=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:20]([CH3:28])=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:18]=[C:9]2[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11117285Ethyl 3-bromo-2-oxobutanoateHCID 178511964HCID 178511964, compound

Product 1

HCID 11316968Ethyl 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-5-methyl-1h-imidazole-4-carboxylateYield 47.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a magnetically stirred solution of above imidamide from step A (2.45 g, 7 mmol) in 30 mL anhydrous toluene were added ethyl 3-bromo-2-oxobutanoate (1.48 g, 7 mmol) and Na2CO3 (0.74 g, 7 mmol). The contents were stirred at 100° C. for 12 hours. The reaction was brought to RT. The reaction mixture was quenched with water and extracted with ethyl acetate. The combined extracts were dried over anhydrous MgSO4, filtered and evaporated under reduced pressure. Purification by column chromatography gave the ester as pale white solid (1.5 g, 46.4%).

Workup

  1. customwas brought to RT
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-50885da7d66244088b39947f56609365
Source dataset
uspto-grants-2014_10
Patent number
US08853205B2

Reaction notes

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