Dimethyl Sulfoxide → HCID 4364549, compound

HRID 620731Notes

Reaction equation

HRID 620731 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].[H-].[Na+].CS(C)=O.F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1>O1CCCC1.O>[C:2](=[N:4][O:5][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)([CH3:3])[CH3:1]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 67180Acetone, oxime

Product 1

HCID 4364549HCID 4364549, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of propanone oxime (30 g, 0.4 mole) in dry tetrahydrofuran (300 ml) was added slowly to a suspension of sodium hydride (10.8 g, 0.45 mole) in dry tetrahydrofuran (50 ml). After gas evolution was complete, dimethylsulphoxide (100 ml) and 4-fluoronitrobenzene (57.85 g, 0.41 mole) were added and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was then poured into water and extracted three times with ether. The combined ether extracts were washed with water, dried (MgSO4) and evaporated to give the title compound which was granulated in hexane and filtered, yield 67 g. A sample (7 g) was recrystallised from ethanol, yield 5 g, m.p. 104°-106°.

Workup

  1. extractionextracted three times with ether
  2. washThe combined ether extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-43d4b39244704dd1bb10451791f4af50
Source dataset
uspto-grants-1989_04
Patent number
US04822793

Reaction notes

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