Acetic Acid → Ammonium Acetate

HRID 373730Notes

Reaction equation

[CH2:1]([N:3]([CH2:25][CH3:26])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:24])[C:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1)[CH3:2].[C:27]([OH:30])(=[O:29])[CH3:28]>>[CH2:25]([N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:24])[C:11]([C:13]2[CH:14]=[CH:15][C:16]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:17][CH:18]=2)=[O:12])=[CH:8][CH:9]=1)[CH3:26].[C:27]([O-:30])(=[O:29])[CH3:28].[NH4+:3]

Participants

Reactant 2

HCID 176Acetic Acid

HCID 4616522Ethanedione, bis[4-(diethylamino)phenyl]-

Product 2

HCID 517165Ammonium Acetate

HCID 4616522Ethanedione, bis[4-(diethylamino)phenyl]-

Procedure

In 100 g of acetic acid, 7.0 g of 1,2-bis(4-diethylaminophenyl)ethane-1,2-dione obtained in above (1), 3.6 g of syringaaldehyde (mfd. by tokyo Kasei Kogyo Co., Ltd.) and 4 g of ammonium acetate were reacted under reflux for 5 hours. After the reaction, 600 ml of water was poured into the reaction solution. The produced viscous residue was separated and the viscous residue was purified by silica gel chromatography (eluent: a mixed solvent of chloroform and methanol) to give 1.6 g of 2-(3,5-dimethoxy-4-hydroxyphenyl)-4,5-bis(4-diethylaminophenyl)imidazole.

Sources & evidence

ORD record: ord-f0a8e9f4baf54912aced21b860f568c9
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05164512

Reaction notes

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