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

HRID 1198848
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HRID 1198848 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-96fe96bcdb2f45a2945650d935620135
출처 데이터셋
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04898607

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