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Sulfuric Acid → 1-(2,2-Dimethyl-3-oxoindan-1-yl)-5-imidazolecarboxylic acid methyl ester

HRID 1198848
Notes
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Reaction equation

HRID 1198848 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]([CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][C:11]2([CH3:20])[CH3:19])[CH:8]=[N:7][CH:6]=1)=[O:4].S(=O)(=O)(O)[OH:22].[NH4+].[NH4+].[O-]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:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:22])[C:11]2([CH3:20])[CH3:19])[CH:8]=[N:7][CH:6]=1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 62648Ammonium PersulfateHCID 218730963-(2,2-dimethyl-indan-1-yl)-3H-imidazole-4-carboxylic acid methyl ester

Product 1

HCID 539208951-(2,2-Dimethyl-3-oxoindan-1-yl)-5-imidazolecarboxylic acid methyl esterYield 60.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 30.0 g of 1-(2,2-dimethylindan-1-yl)-5-imidazolecarboxylic acid methyl ester, 150 ml of water and 17 g of sulfuric acid is heated to +80° C. Within a period of 1.5 hours a solution of 114 g of ammonium peroxodisulfate is added dropwise thereto. When the reaction is complete, the solution is cooled to +7° C. and adjusted to pH 3 by the addition of 30% sodium hydroxide solution. The solution is extracted twice using 200 ml of methylene chloride each time, and the organic phase is dried over sodium sulfate and concentrated to dryness by evaporation. The residue is taken up in a small amount of methylene chloride, and ether is added. The resulting suspension is filtered, the filtrate is concentrated by evaporation and the residue is crystallised from an ether/hexane mixture. 19 g of 1-(2,2-dimethyl-3-oxoindan-1-yl)-5-imidazolecarboxylic acid methyl ester having a melting point of 104°-108° C. are obtained.

Workup

  1. temperatureis heated to +80° C
  2. temperaturethe solution is cooled to +7° C.
  3. extractionThe solution is extracted twice
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. concentrationconcentrated to dryness by evaporation
  6. additionis added
  7. filtrationThe resulting suspension is filtered
  8. concentrationthe filtrate is concentrated by evaporation
  9. customthe residue is crystallised from an ether/hexane mixture

Sources & evidence

ORD record
ord-96fe96bcdb2f45a2945650d935620135
Source dataset
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04898607

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes