Hydrogen Bromide → 1,3-dihydro-4-(4-methoxybenzoyl)-5-(methoxymethyl)-2H-imidazol-2-one

HRID 370552Notes

Reaction equation

Br[CH2:2][C:3]1[N:7](C(=O)C)[C:6](=[O:11])[N:5](C(=O)C)[C:4]=1[C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[CH3:25][OH:26].Br>O1CCCC1>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:15]([C:4]2[NH:5][C:6](=[O:11])[NH:7][C:3]=2[CH2:2][O:26][CH3:25])=[O:24])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4.0 g of 5-(bromomethyl)-1,3-diacetyl-1,3-dihydro-4-(4-methoxybenzoyl)-2H-imidazol-2-one in 50 ml of dry tetrahydrofuran is cooled to -78° C. under argon, 1.0 ml of dry methanol is added by syringe, and the solution is allowed to warm to 25° C. over 1.5 hours. Concentrated hydrobromic acid (1 ml) is then added and the mixture is stirred at 25° C. overnight. The solvent is then evaporated and the residual solid is recrystallized twice from a mixture of methanol and water to give 1,3-dihydro-4-(4-methoxybenzoyl)-5-(methoxymethyl)-2H-imidazol-2-one melting at about 211°-212° C. with decomposition. This compound has the following structural formula: ##STR6##

Workup

customThe solvent is then evaporated
customthe residual solid is recrystallized twice from a mixture of methanol and water

Sources & evidence

ORD record: ord-5d07ea2dc42b439b9ea33dbac79487aa
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04526981

Reaction notes

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