Potassium Carbonate → 2-Isopropyl-5,6-dihydro-1H-benzo[d]imidazol-7(4H)-one

HRID 1946519Notes

Reaction equation

HRID 1946519 reaction equation
Br[C:2]1[C:3](=O)[CH2:4][CH2:5][CH2:6][C:7]=1[O:8]C.Cl.[CH3:12][CH:13]([CH3:17])[C:14](=[NH:16])[NH2:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.ClCCl>[CH3:12][CH:13]([C:14]1[NH:16][C:3]2[CH2:4][CH2:5][CH2:6][C:7](=[O:8])[C:2]=2[N:15]=1)[CH3:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27820532-Methylpropanimidamide hydrochlorideHCID 109981422-Bromo-3-methoxycyclohex-2-en-1-one

Product 1

HCID 584601782-Isopropyl-5,6-dihydro-1H-benzo[d]imidazol-7(4H)-oneYield 53.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2-bromo-3-(methyloxy)-2-cyclohexen-1-one (1.88 g) in anhydrous N,N-dimethylformamide (35 mL) at ambient temperature was added solid 2-methylpropanimidamide hydrochloride (1.349 g) and potassium carbonate (3.17 g). The reaction was then heated to 100° C. under an atmosphere of nitrogen for 3 hr. The reaction was diluted with dichloromethane (100 mL) the resultant solid was removed by filtration. The filtrate was concentrated in vacuo. The sample was loaded in dichloromethane and purified on silica using a 0-25% methanol-dichloromethane gradient. The appropriate fractions were combined and evaporated in vacuo to give the required product (867 mg). LC/MS MH+ 179, Rt 0.34 min (2 min run).

Workup

  1. customwas removed by filtration
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified on silica using a 0-25% methanol-dichloromethane gradient
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-aada70e08bfa4bd29ebf07730fc0862a
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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