Citric Acid → HCID 178426893, compound

HRID 1722055Notes

Reaction equation

HRID 1722055 reaction equation
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

Participants

7

Reactant 5

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

Product 1

HCID 178426893HCID 178426893, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6c48de15d70a433c9fb7ebedeae738d6
Source dataset
uspto-grants-1989_08
Patent number
US04853405

Reaction notes

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