Iodoethane → 4-Ethyl-8-(3-(trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylene-3,5(4H)-dione

HRID 2050513Notes

Reaction equation

HRID 2050513 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([C:9]2[N:19]3[C:20]4[N:12]([C:13](=[O:22])[NH:14][C:15](=[O:21])[C:16]=4[CH:17]=[N:18]3)[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].I[CH2:28][CH3:29]>CN(C)C=O.C(Cl)(Cl)Cl>[CH2:28]([N:14]1[C:13](=[O:22])[N:12]2[C:20]3[N:19]([C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:23])[F:24])[CH:4]=4)=[CH:10][CH2:11]2)[N:18]=[CH:17][C:16]=3[C:15]1=[O:21])[CH3:29]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 150440768-(3-(Trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylene-3,5(4H)-dione

Product 1

HCID 200583754-Ethyl-8-(3-(trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylene-3,5(4H)-dione

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 5.0 g of 8-(3-(trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylene-3,5(4H)-dione (prepared as described in Example 14) in 50 ml of dry N,N-dimethylformamide, under nitrogen, is added 800 mg of 60 percent sodium hydride (dispersion in mineral oil). The mixture is stirred at room temperature for 2 hours, then 10 ml of iodoethane is added and stirring is continued for 48 hours. The reaction mixture is evaporated to dryness, then treated with water, and the gummy solid which is isolated is dissolved in chloroform and the extract dried over anhydrous sodium sulfate. Evaporation gives an oil which is triturated with diethyl ether-hexane to provide a yellow solid which is collected by filtration to give 2.0 g of the desired product as a white solid. The product is recrystallized from isopropyl alcohol, mp 161-163° C.

Workup

  1. stirringstirring
  2. waitis continued for 48 hours
  3. customThe reaction mixture is evaporated to dryness
  4. additiontreated with water
  5. customthe gummy solid which is isolated
  6. dry with materialthe extract dried over anhydrous sodium sulfate
  7. customEvaporation
  8. customgives an oil which
  9. customis triturated with diethyl ether-hexane
  10. customto provide a yellow solid which
  11. filtrationis collected by filtration

Sources & evidence

ORD record
ord-29f8a411b7dd4c85a46fb10dcf333c92
Source dataset
uspto-grants-1991_05
Patent number
US05013737

Reaction notes

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