Sodium Hydroxide → 1-(2,2-Dimethyl-4-oxotetralin-1-yl)-5-imidazolecarboxylic acid methyl ester

HRID 5773Notes

Reaction equation

HRID 5773 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].[OH-:22].[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:22])[CH2:12][C:11]2([CH3:21])[CH3:20])[CH:8]=[N:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 200684021-(2,2-Dimethyltetralin-1-yl)-5-imidazolecarboxylic acid methyl ester

Product 1

HCID 249960101-(2,2-Dimethyl-4-oxotetralin-1-yl)-5-imidazolecarboxylic acid methyl esterYield 28.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

142 g of 1-(2,2-dimethyl-tetralin-1-yl)-5-imidazolecarboxylic acid methyl ester are dispersed in 1 liter of deionisized water. The suspension is heated to +87° C., and within a period of 1.5 hours a total of 335 g of ammoniaperoxodisulfate is added portionwise in such a manner, that the temperature does not exceed +90° C. After cooling the reaction mixture to +15° C., the pH-value is adjusted to pH 4 by addition of 335 g of a sodium hydroxide solution 30%. The mixture is extracted with 500 ml of methylene chloride. The organic phase is separated, dried with sodium sulfate, treated with activated carbon and concentrated. Crystallisation of the residue from diethyl ether yields 42 g of 1-(2,2-dimethyl-4-oxo-tetralin-1-yl)-5-imidazolecarboxylic acid methyl ester, having a melting point of 93°-95° C.

Workup

  1. temperatureThe suspension is heated to +87° C.
  2. additionwithin a period of 1.5 hours a total of 335 g of ammoniaperoxodisulfate is added portionwise in such a manner
  3. customdoes not exceed +90° C
  4. temperatureAfter cooling the reaction mixture to +15° C.
  5. extractionThe mixture is extracted with 500 ml of methylene chloride
  6. customThe organic phase is separated
  7. dry with materialdried with sodium sulfate
  8. additiontreated with activated carbon
  9. concentrationconcentrated
  10. customCrystallisation of the residue from diethyl ether

Sources & evidence

ORD record
ord-37a0638f1dc84d4298b53e5aaef50245
Source dataset
uspto-grants-1993_09
Patent number
US05246915

Reaction notes

Loading…