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

HRID 1946521Notes

Reaction equation

Br[C:2]1[C:3](=O)[CH2:4][CH2:5][CH2:6][C:7]=1[O:8]CC.Cl.[CH3:13][CH:14]([CH3:18])[C:15](=[NH:17])[NH2:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:13][CH:14]([C:15]1[NH:17][C:3]2[CH2:4][CH2:5][CH2:6][C:7](=[O:8])[C:2]=2[N:16]=1)[CH3:18]

Participants

Conditions

Temperature: 80 °C

Procedure

To 2-bromo-3-(ethyloxy)-2-cyclohexen-1-one (38.8 g) in a 1 L round-bottom flask in N,N-Dimethylformamide (DMF) (500 mL) was added 2-methylpropanimidamide hydrochloride (26.1 g) and potassium carbonate (61.2 g). The suspension was then stirred at 80° C. under nitrogen for 2 h. The mixture was filtered and as much DMF as possible was evaporated off under high vacuum. The sample was loaded in dichloromethane and purified by column chromatography over silica using a 0-30% methanol-dichloromethane gradient. The appropriate fractions were combined and evaporated in vacuo to give the required product 14.2 g as a brown solid. LC/MS MH+ 179, Rt 1.4 min (5 min run).

Workup

filtrationThe mixture was filtered and as much DMF
customas possible was evaporated off under high vacuum
custompurified by column chromatography over silica using a 0-30% methanol-dichloromethane gradient
customevaporated in vacuo

Sources & evidence

ORD record: ord-f4dea2f51049433fa090e9340e9a3f37
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399444B2

Reaction notes

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