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

HRID 5775
ノート
印刷プレビュー

反応式

HRID 5775 の反応式
[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].[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 30 g of 1-(2,2-dimethyl-indan-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 an aqueous solution of 114 g of ammoniaperoxodisulfate is added dropwise. The reaction mixture is cooled to +7° C. and the pH-value is adjusted to pH 3 by addition of a 30% sodium hydroxide solution. The mixture is twice extracted with 200 ml of methylene chloride. The combined organic extracts are dried with sodium sulfate and concentrated to dryness. The residue is taken up with a small amount of methylene chloride and diluted with diethyl ether. The resulting suspension is filtered and the filtrate is concentrated and crystallized from a diethyl ether/hexane mixture affording 19 g of 1-(2,2-dimethyl-3-oxo-indan-1-yl)-5-imidazolecarboxylic acid methyl ester, mp. 104°-108° C.

後処理

  1. temperatureis heated to +80° C
  2. additionWithin a period of 1.5 hours an aqueous solution of 114 g of ammoniaperoxodisulfate is added dropwise
  3. temperatureThe reaction mixture is cooled to +7° C.
  4. extractionThe mixture is twice extracted with 200 ml of methylene chloride
  5. dry with materialThe combined organic extracts are dried with sodium sulfate
  6. concentrationconcentrated to dryness
  7. additiondiluted with diethyl ether
  8. filtrationThe resulting suspension is filtered
  9. concentrationthe filtrate is concentrated
  10. customcrystallized from a diethyl ether/hexane mixture

出典と根拠

ORDレコード
ord-5e6d61be575e48c1b3148f75190618fb
出典データセット
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05246915

反応ノート

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