Trimethylamine → 2,3-dihydro-5-(4-methoxybenzoyl)-N,N,N-trimethyl-2-oxo-1H-imidazole-4-methanaminium bromide sesquihydrate

HRID 1702488Notes

Reaction equation

[Br:1][CH2:2][C:3]1[N:7](C(=[O:10])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][N:26]([CH3:28])[CH3:27]>O1CCCC1>[OH2:10].[Br-:1].[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][N+:26]([CH3:28])([CH3:27])[CH3:25])=[O:24])=[CH:21][CH:20]=1.[OH2:10].[OH2:10].[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][N+:26]([CH3:28])([CH3:27])[CH3:25])=[O:24])=[CH:21][CH:20]=1.[Br-:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold solution (0° C.) of 6.0 g of 5-(bromomethyl)-1,3-diacetyl-1,3-dihydro-4-(4-methoxybenzoyl)-2H-imidazol-2-one in 50 ml of dry tetrahydrofuran is added gaseous trimethylamine over a period of 15 minutes. The mixture is stirred at 0° C. for 15 minutes and the solvent is then evaporated under reduced pressure. To the residue is added 30 ml of 30% hydrobromic acid in acetic acid and the solution is allowed to stand at 25° C. for 1 hour. The solvent is then evaporated under reduced pressure and the residue is first crystallized from water and then recrystallized from ethanol to give 2,3-dihydro-5-(4-methoxybenzoyl)-N,N,N-trimethyl-2-oxo-1H-imidazole-4-methanaminium bromide sesquihydrate melting at about 148°-150° C. with decomposition.

Workup

customthe solvent is then evaporated under reduced pressure
additionTo the residue is added 30 ml of 30% hydrobromic acid in acetic acid
waitto stand at 25° C. for 1 hour
customThe solvent is then evaporated under reduced pressure
customthe residue is first crystallized from water
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-094ad9b9c99440b0b2f97466d38cdf70
Source dataset: uspto-grants-1983_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04381393

Reaction notes

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