Water → HCID 13668110, compound

HRID 1981467Notes

Reaction equation

HRID 1981467 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH:12]=O)=O)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[NH2:14]/[C:15](/[C:20]#[N:21])=[C:16](\[NH2:19])/[C:17]#[N:18].O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:20]([C:15]1[C:16]([C:17]#[N:18])=[N:19][C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=2)=[CH:12][N:14]=1)#[N:21]

Participants

6

Reactant 3

HCID 962WaterHCID 2723951DiaminomaleonitrileHCID 13512486HCID 13512486, compound

Product 1

HCID 13668110HCID 13668110, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

This 4-propylphenylglyoxal (8.0 g, 0.05 mol) and diaminomaleonitrile (5.4 g, 0.05 mol) were dissolved in benzene (50 ml), followed by adding p-toluenesulfonic acid (0.05 g) to the solution, reacting them on heating under reflux for 3 hours, while distilling off water formed, allowing the reaction liquid to cool down to room temperature after completion of the reaction, adding water (50 ml), separating the resulting two layers, twice washing the benzene solution with 5% sodium bicarbonate solution (50 ml), further washing it with water, drying it with anhydrous sodium sulfate, distilling off benzene from the solution, and recrystallizing a remaining solid material from ethanol (10 ml) to obtain the objective product (8.9 g).

Workup

  1. temperatureon heating
  2. temperatureunder reflux for 3 hours
  3. distillationwhile distilling off water
  4. customformed
  5. customthe reaction liquid
  6. customafter completion of the reaction
  7. customseparating the resulting two layers
  8. washtwice washing the benzene solution with 5% sodium bicarbonate solution (50 ml)
  9. washfurther washing it with water
  10. dry with materialdrying it with anhydrous sodium sulfate
  11. distillationdistilling off benzene from the solution
  12. customrecrystallizing a remaining solid material from ethanol (10 ml)

Sources & evidence

ORD record
ord-f46a80dd226a4385b36088d4a4806195
Source dataset
uspto-grants-1986_06
Patent number
US04592857

Reaction notes

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