Sodium Hydroxide → 1-(2,2-Dimethyl-4-oxotetralin-1-yl)-5-imidazolecarboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][C:11]2([CH3:21])[CH3:20])[CH:8]=[N:7][CH:6]=1)=[O:4].[NH4+].[NH4+].[O-:24]S(OOS([O-])(=O)=O)(=O)=O.[OH-].[Na+]>O>[CH3:1][O:2][C:3]([C:5]1[N:9]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:24])[CH2:12][C:11]2([CH3:21])[CH3:20])[CH:8]=[N:7][CH:6]=1)=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
142 g of 1-(2,2-dimethyltetralin-1-yl)-5-imidazolecarboxylic acid methyl ester are suspended in 1 liter of distilled water. The suspension is heated to +87° C. and, while stirring, a total of 335 g of ammonium peroxodisulfate is added in portions thereto within a period of 1.5 hours in such a manner that the temperature does not exceed +90° C. After the reaction mixture has been cooled to +15° C., the pH value is adjusted to pH 4 by the addition of approximately 335 g of 30% sodium hydroxide solution and the whole is extracted with 500 ml of methylene chloride. The organic phase is separated off, dried over sodium sulfate, treated with activated carbon and concentrated by evaporation. Crystallisation of the residue from ether yields 42 g of 1-(2,2-dimethyl-4-oxotetralin-1-yl)-5-imidazolecarboxylic acid methyl ester having a melting point of 93°-95° C.
Workup
- temperatureThe suspension is heated to +87° C.
- temperatureAfter the reaction mixture has been cooled to +15° C.
- extractionthe whole is extracted with 500 ml of methylene chloride
- customThe organic phase is separated off
- dry with materialdried over sodium sulfate
- additiontreated with activated carbon
- concentrationconcentrated by evaporation
- customCrystallisation of the residue from ether
Sources & evidence
- ORD record
- ord-cf1e5c14f15142508541f085b773aefa
- Source dataset
- uspto-grants-1991_03
- Patent number
- US05000777
Reaction notes
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