Ethyl bromopyruvate → HCID 69416371, compound

HRID 1296357Notes

Reaction equation

HRID 1296357 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)=[NH:5].C(=O)(O)[O-].[Na+].[CH2:24]([O:26][C:27](=[O:32])[C:28](=[O:31])[CH2:29]Br)[CH3:25]>CC(O)C>[CH2:24]([O:26][C:27]([C:28]1([OH:31])[CH2:29][N:6]([C:7]2[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=2)[C:4]([C:3]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:2]=2[Cl:1])=[N:5]1)=[O:32])[CH3:25]

Participants

5

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 178512018HCID 178512018, compound

Product 1

HCID 69416371HCID 69416371, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2,4-dichloro-N-(4-chloro-phenyl)-benzamidine I-7a (34 g, 113.5 mmol) and sodium bicarbonate (19.1 g, 227 mmol) in 2-propanol (600 ml) was treated with 3-bromo-2-oxo-propionic acid ethyl ester (20 ml, 158.9 mmol). The reaction mixture was heated to 85° C. overnight, and the solvent was removed in vacuo. The residue was partitioned between methylene chloride and water, and the layers were separated. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was triturated with ether/hexanes (1:3), and the yellow solid, 1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-4-hydroxy-4,5-dihydro-1H-imidazole-4-carboxylic acid ethyl ester I-7b (45 g, 96%), was collected by filtration.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between methylene chloride and water
  3. customthe layers were separated
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was triturated with ether/hexanes (1:3)
  7. filtrationthe yellow solid, 1-(4-chloro-phenyl)-2-(2,4-dichloro-phenyl)-4-hydroxy-4,5-dihydro-1H-imidazole-4-carboxylic acid ethyl ester I-7b (45 g, 96%), was collected by filtration

Sources & evidence

ORD record
ord-4a3021e7d0764879a95d4a93157f5395
Source dataset
uspto-grants-2007_07
Patent number
US07247628B2

Reaction notes

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