Potassium Carbonate → HCID 59497704, compound

HRID 1747366Notes

Reaction equation

HRID 1747366 reaction equation
[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])([CH3:3])=[CH2:2].[CH3:14][O:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[C:18]=1[CH2:26]Br.C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CN(C=O)C>[CH3:14][O:15][C:16](=[O:28])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[C:18]=1[CH2:26][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:4]([C:1]([CH3:3])=[CH2:2])[C:5]1=[O:13]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-oneHCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoate

Product 1

HCID 59497704HCID 59497704, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-isopropenyl-2-benzimidazolidinone (200 mg, 1.1 mmol) in DMF (10 mL) were added methyl-2-bromomethyl-3-nitrobenzoate (472 mg, 1.7 mmol) and K2CO3 (317 mg, 2.3 mmol) at room temperature. The solution was heated to 80 C for 2 hours. The solution was cooled down and sat. NH4Cl solution was added. The solution was extracted with EtOAc. The combined organic layer was dried with MgSO4 and was filtered. The filtrate was concentrated and the residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent to afford the desirable product 2-(3-Isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-3-nitro-benzoic acid methyl ester (395 mg, 94%) as a pale yellow foam.

Workup

  1. temperatureThe solution was heated to 80 C for 2 hours
  2. temperatureThe solution was cooled down
  3. extractionThe solution was extracted with EtOAc
  4. dry with materialThe combined organic layer was dried with MgSO4
  5. filtrationwas filtered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-f095eeb613ca4efdbd90823418afdcac
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…