Toluene → 2-Cyano-2-cyclohexylidene-acetamide

HRID 130574Notes

Reaction equation

HRID 130574 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([CH2:10][C:11]([NH2:13])=[O:12])#[N:9].C1(=O)CCCCC1.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[C:1]1(=[C:10]([C:8]#[N:9])[C:11]([NH2:13])=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7898CyanoacetamideHCID 7967CyclohexanoneHCID 517165Ammonium Acetate

Product 1

HCID 2636542-Cyano-2-cyclohexylidene-acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

600 ml of toluene, 200 g of cyanoacetamide, 193 g of cyclohexanone, 15 g of ammonium acetate and 24 g of acetic acid are placed in a 2 litre flask equipped with a mechanical stirrer, thermometer and Dean-Stark trap connected to a condenser, under nitrogen flow. The mixture is heated under reflux, simultaneously separating the water by distilling the water-toluene azeotrope. The separated water is collected in the Dean-Stark trap and removed at suitable time intervals. After 2 hours, on completion of the azeotropic distillation, it is cooled to 70° C., washed with 400 ml of a saturated sodium bicarbonate solution and cooled to 15° C. The precipitated solid is filtered off, washed with 70 ml of toluene, then 70 ml of water and dried in an oven at 40° C. under vacuum. 213 g of 2-cyclohexylidene-2-cyanoacetamide are obtained.

Workup

  1. customequipped with a mechanical stirrer
  2. customthermometer and Dean-Stark trap connected to a condenser, under nitrogen
  3. temperatureThe mixture is heated
  4. temperatureunder reflux
  5. customsimultaneously separating the water
  6. distillationby distilling the water-toluene azeotrope
  7. customThe separated water is collected in the Dean-Stark trap
  8. customremoved at suitable time intervals
  9. distillationon completion of the azeotropic distillation, it
  10. washwashed with 400 ml of a saturated sodium bicarbonate solution
  11. temperaturecooled to 15° C
  12. filtrationThe precipitated solid is filtered off
  13. washwashed with 70 ml of toluene
  14. dry with material70 ml of water and dried in an oven at 40° C. under vacuum

Sources & evidence

ORD record
ord-16ee264c07114d4ba2ef5244e24ac618
Source dataset
uspto-grants-2008_06
Patent number
US07381823B2

Reaction notes

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