Benzenamine, 2,6-dimethoxy- → 5-(4-Amino-3,5-dimethoxyphenyl)-5-hydroxybarbituric acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:4]=1[NH2:5].O.O.O.O.[NH:16]1[C:24](=[O:25])[C:22](=[O:23])[C:20](=[O:21])[NH:19][C:17]1=[O:18]>O>[NH2:5][C:4]1[C:6]([O:10][CH3:11])=[CH:7][C:8]([C:22]2([OH:23])[C:20](=[O:21])[NH:19][C:17](=[O:18])[NH:16][C:24]2=[O:25])=[CH:9][C:3]=1[O:2][CH3:1]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
25 g of 2,6-dimethoxyaniline were added to a solution of 35 g of alloxan tetrahydrate in 120 ml of water. While stirring vigorously, the initially heterogeneous mixture changed after one hour into a brown solution from which grey crystals separated after a short time. The reaction mixture was stirred at room temperature for an additional 24 hours until dimethoxyaniline was no longer detectable according to thin-layer chromatography (cyclohexane/ethyl acetate/water=60:30:1). The reaction mixture was suction filtered, the residue on the suction filter was suspended with 4 portions of water to 80 ml and sucked dry. The solid was dried at 100°/16 mbar for 16 hours. There were obtained 44.2 g of 5-(4-amino-3,5-dimethoxyphenyl)-5-hydroxybarbituric acid as a light grey powder of m.p. 240°-243° (under decomposition). For purification, the powder can be recrystallized from 1-butanol, there being obtained a product of m.p. 242°-244° (decomposition).
Workup
- customseparated after a short time
- stirringThe reaction mixture was stirred at room temperature for an additional 24 hours until dimethoxyaniline
- filtrationfiltered
- filtrationthe residue on the suction filter
- customsucked dry
- customThe solid was dried at 100°/16 mbar for 16 hours
Sources & evidence
- ORD record
- ord-0cd81c599a374e4b8c37613dc6cc0a5d
- Source dataset
- uspto-grants-1988_10
- Patent number
- US04775756
Reaction notes
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