Dimethylformamide → HCID 13069836, compound

HRID 1703165Notes

Reaction equation

HRID 1703165 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[CH2:4][C:5]#N.[OH-].[K+].CN(C)C=[O:17].[O:19]1[CH:21]([CH2:22][CH3:23])[CH2:20]1>O>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[CH:4]1[CH2:20][CH:21]([CH2:22][CH3:23])[O:19][C:5]1=[O:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78341,2-EpoxybutaneHCID 14797Potassium HydroxideHCID 805662,4-Dichlorophenylacetonitrile

Product 1

HCID 13069836HCID 13069836, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 186 g. (1 mole) of 2,4-dichlorobenzyl cyanide and 60 g. (1.1 mole) of powdered potassium hydroxide in 400 ml. of dry dimethyl formamide is added 75 g. (1 mole) of 1,2-epoxy butane dropwise at 10° C. The resulting brown reaction mixture is stirred at room temperature overnight. It is then poured into water and extracted with ether. The combined ether extracts are washed with water, 5% sodium chloride solution and dried over magnesium sulfate. Solvent is evaporated to give 228 g. of a brown oil which is assigned the iminolactone structure due to strong ir absorption at 1680 cm-1. This material is redissolved in toluene and 300 ml. 25% hydrochloric acid are added. The mixture is heated over a steam bath for two hours. The organic layer is separated and washed with water, saturated sodium chloride solution and dried over magnesium sulfate. Solvent is evaporated to give a light yellow oil which is further purified by vacuum distillation (150° C./0.2 mm) to give 200 g. of desired product.

Workup

  1. additionTo a mixture of 186 g
  2. customdropwise at 10° C
  3. extractionextracted with ether
  4. washThe combined ether extracts are washed with water, 5% sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customSolvent is evaporated
  7. customto give 228 g
  8. customdue to strong ir absorption at 1680 cm-1
  9. dissolutionThis material is redissolved in toluene
  10. addition25% hydrochloric acid are added
  11. temperatureThe mixture is heated over a steam bath for two hours
  12. customThe organic layer is separated
  13. washwashed with water, saturated sodium chloride solution
  14. dry with materialdried over magnesium sulfate
  15. customSolvent is evaporated
  16. customto give a light yellow oil which
  17. distillationis further purified by vacuum distillation (150° C./0.2 mm)
  18. customto give 200 g

Sources & evidence

ORD record
ord-05d02b7b43554064baec0f2309ef45f1
Source dataset
uspto-grants-1982_09
Patent number
US04351839

Reaction notes

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