Sodium hydride → 2-Nitro-6-(2-phenoxyethoxy)benzonitrile

HRID 973064Notes

Reaction equation

HRID 973064 reaction equation
[O:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[H-].[Na+].[N+]([C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:18]=1[C:19]#[N:20])([O-])=O>CS(C)=O>[N+:25]([C:21]1[CH:22]=[CH:23][CH:24]=[C:17]([O:10][CH2:9][CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:18]=1[C:19]#[N:20])([O-:27])=[O:26]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 31236PhenoxyethanolHCID 520718DinitrobenzonitrileHCID 5360545Sodium

Product 1

HCID 122648282-Nitro-6-(2-phenoxyethoxy)benzonitrileYield 99.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

2-Phenoxyethanol (4.15 ml, 0.033 mole) is added to dimethylsulfoxyl sodium prepared from 1.39 g of 57 percent sodium hydride and 40 ml dimethylsulfoxide, giving a mixture of the solid salt of the alcohol after about 20 minutes. This mixture is added to a solution of 5.8 g (0.030 mole) 2,6-dinitrobenzonitrile in 20 ml of dimethylsulfoxide at 30-40° C., and the resulting purple solution is stirred over night at room temperature. The solvent is removed at 70° C. on a rotary evaporator, and the residue is triturated with water. A solid is filtered off and it is dissolved in ethylacetate. The ethylacetate solution is washed twice with H2O, brine, and dried with calcium sulfate. Evaporation of the ethylacetate, gives 8.5 g of 2-nitro-6(2-phenoxyethoxy)benzonitrile, which is crystallized from 200 ml ethyl alcohol, giving 6 g, m.p. 129°-137.5° C.

Workup

  1. customgiving
  2. customThe solvent is removed at 70° C. on a rotary evaporator
  3. customthe residue is triturated with water
  4. filtrationA solid is filtered off
  5. dissolutionit is dissolved in ethylacetate
  6. washThe ethylacetate solution is washed twice with H2O, brine
  7. dry with materialdried with calcium sulfate
  8. customEvaporation of the ethylacetate

Sources & evidence

ORD record
ord-f6771c83b5064a608e3fb197da353db1
Source dataset
uspto-grants-1977_10
Patent number
US04054661

Reaction notes

Loading…