Acetone → HCID 21319892, compound

HRID 262085Notes

Reaction equation

HRID 262085 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([N+:11]([O-:13])=[O:12])=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]=2[CH:20]=1.CC(C)=O.C(O)C.[C-:28]#[N:29].[Na+]>O>[C:28]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([N+:11]([O-:13])=[O:12])=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]=2[CH:20]=1)#[N:29]

Participants

6

Reactant 4

HCID 180AcetoneHCID 702EthanolHCID 8929Sodium CyanideHCID 13531604HCID 13531604, compound

Product 1

HCID 21319892HCID 21319892, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-bromomethyl-2-nitro-3-phenylbenzofuran (5 g., 0.015 mole) in 95 ml. of acetone is treated with 20 ml. of ethanol, and the mixture is heated to its reflux temperature. To this mixture is added 0.015 mole of sodium cyanide dissolved in 9 ml. of water, and refluxing is continued for about two hours. The mixture is evaporated under vacuum, then dichloromethane and water are added to the residue. The organic layer is separated, washed with water and dried. The organic layer is then evaporated under vacuum. The residue is purified by eluting twice with benzene through a silica gel column, followed by refluxing in 30 ml. of diethyl ether. The yellow precipitate is separated by filtration and recrystallized twice from benzene to provide 5-cyanomethyl-2-nitro-3-phenylbenzofuran, m.p. 166°-168° C.

Workup

  1. temperaturereflux temperature
  2. dissolutiondissolved in 9 ml
  3. customThe mixture is evaporated under vacuum
  4. additiondichloromethane and water are added to the residue
  5. customThe organic layer is separated
  6. washwashed with water
  7. customdried
  8. customThe organic layer is then evaporated under vacuum
  9. customThe residue is purified
  10. washby eluting twice with benzene through a silica gel column
  11. temperatureby refluxing in 30 ml
  12. customThe yellow precipitate is separated by filtration
  13. customrecrystallized twice from benzene

Sources & evidence

ORD record
ord-fb4c54cfdf244d80b77c4e87a8dfc74c
Source dataset
uspto-grants-1979_05
Patent number
US04153619

Reaction notes

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