Dimethylamine → 4-[(dimethylamino)methyl]-1,3-dihydro-5-(4-methoxybenzoyl)-2H-imidazol-2-one

HRID 1702487Notes

Reaction equation

Br[CH2:2][C:3]1[NH:7][C:6](=[O:8])[NH:5][C:4]=1[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.[CH3:19][NH:20][CH3:21]>C(O)C>[CH3:19][N:20]([CH2:2][C:3]1[NH:7][C:6](=[O:8])[NH:5][C:4]=1[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[CH3:21]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 3.1 g of 5-(bromomethyl)-1,3-dihydro-4-(4-methoxybenzoyl)-2H-imidazol-2-one, 12 ml of 30% aqueous dimethylamine and 24 ml of ethanol is stirred at 25° C. for 2 hours. The solvent is then evaporated from the mixture under reduced pressure and the resultant residue is recrystallized twice from ethanol to give 4-[(dimethylamino)methyl]-1,3-dihydro-5-(4-methoxybenzoyl)-2H-imidazol-2-one melting at about 165°-167° C. with decomposition.

Workup

customThe solvent is then evaporated from the mixture under reduced pressure
customthe resultant residue is recrystallized twice from ethanol

Sources & evidence

ORD record: ord-c7ff0616b2e04d06beea01efd75289ad
Source dataset: uspto-grants-1983_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04381393

Reaction notes

Loading…