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Citric Acid → HCID 178426893、化合物

HRID 1722055
ノート
印刷プレビュー

反応式

HRID 1722055 の反応式
C([O:3][C:4]([C:6]1[C:15]2[C:10]3[C:11](=[C:16]4[C:20]([C:9]=3[CH:8]([CH3:21])[CH:7]=1)=[CH:19][N:18]=[N:17]4)[CH:12]=[CH:13][CH:14]=2)=O)C.C1(=O)C2=C3C(=CC=C2)C=CC=C3C1.[H-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[CH3:50][S:51]([CH3:53])=[O:52]>O1CCCC1>[CH3:21][CH:8]1[CH:7]=[C:6]([C:4](=[O:3])[CH2:50][S:51]([CH3:53])=[O:52])[C:15]2[C:10]3[C:11](=[C:16]4[C:20]([C:9]1=3)=[CH:19][N:18]=[N:17]4)[CH:12]=[CH:13][CH:14]=2
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 311Citric AcidHCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 752291-AcenaphthenoneHCID 867432763-Ethoxycarbonyl-1-methyl-1H-acenaphthyleno[1,2-c]pyrazole

生成物 1

HCID 178426893HCID 178426893、化合物

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

3-Ethoxycarbonyl-1-methyl-1H-acenaphthyleno[1,2-c]pyrazole (2g), mp 107°-109° C., prepared according to Example 1 starting from acenaphthen-1-one, is dissolved in anhydrous tetrahydrofuran (45 ml) and added dropwise, under stirring, at a temperature varying between 10° C. and 20° C., to a solution of methylsulfinyl carbanion, obtained by reacting 50% sodium hydride (0.7 g) with anhydrous dimethylsulfoxide (30 ml) at 70° C. for 1 hour. The reaction mixture is kept under stirring at room temperature for 1 hour, then is diluted with ice water and acidified with citric acid to pH 4. The precipitate is extracted with ethyl acetate and the organic solution evaporated to dryness in vacuo. The residue is purified over a flash column using toluene/ethanol/diethylamine 100/10/1.5 as eluent. Washings with ethanol give 0.45 g of 1-methyl-3-methylsulfinylacetyl-1H-acenaphthyleno[1,2-c]pyrazole, mp 220°-230° C. dec., NMR (DMSOd6) δppm: 2.76 (s)(3H, --SOCH3), 4.16 (s)(3H, =N--CH3), 4.57 (s)(2H, --COCH2SO--), 7.5-8.70 (m) (6H, phenyl protons).

後処理

  1. additionadded dropwise
  2. customobtained
  3. customat 70° C.
  4. customfor 1 hour
  5. stirringunder stirring at room temperature for 1 hour
  6. extractionThe precipitate is extracted with ethyl acetate
  7. customthe organic solution evaporated to dryness in vacuo
  8. customThe residue is purified over a flash column
  9. washWashings with ethanol

出典と根拠

ORDレコード
ord-6c48de15d70a433c9fb7ebedeae738d6
出典データセット
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04853405

反応ノート

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