Sulfuric Acid → 3-Amino-2-cyano-3-(dipropylamino)propenenitrile

HRID 616507Notes

Reaction equation

HRID 616507 reaction equation
[C:1]([C-:3]([C:6]#[N:7])[C:4]#[N:5])#[N:2].[K+].S(=O)(=O)(O)O.[CH2:14]([NH:17][CH2:18][CH2:19][CH3:20])[CH2:15][CH3:16]>O.C(OCC)C>[NH2:2][C:1]([N:17]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:15][CH3:16])=[C:3]([C:6]#[N:7])[C:4]#[N:5]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 8902DipropylamineHCID 10964525Potassium Tricyanomethanide

Product 1

HCID 859420343-Amino-2-cyano-3-(dipropylamino)propenenitrileYield 83.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

In the manner of Example VI, part C, 25 g of potassium tricyanomethanide in 75 ml of water and 100 ml of diethyl ether were treated with 19 g of concentrated sulfuric acid to give an ether solution of HN=C=C(CN)2. The ether solution was treated with 19.6 g of dipropylamine and the mixture allowed to stand for 1/2 hour. The ether was removed by distillation under reduced pressure and the residue heated to 150°. To the hot residue were added 500 ml of aqueous ethanol and the mixture was boiled vigorously for 15 minutes. The mixture was again concentrated and the residue heated at 150° for about 16 hours. The mixture was dissolved in aqueous ethanol, treated with activated charcoal and chilled for two days at about 5°. The separated solid was collected by filtration and dried to give 31 g of 3-amino-2-cyano-3-(dipropylamino)propenenitrile, m.p. 100°-105° from toluene. The ir and nmr spectra were consistent with the assigned structure.

Workup

  1. customThe ether was removed by distillation under reduced pressure
  2. temperaturethe residue heated to 150°
  3. additionTo the hot residue were added 500 ml of aqueous ethanol
  4. waitthe mixture was boiled vigorously for 15 minutes
  5. concentrationThe mixture was again concentrated
  6. temperaturethe residue heated at 150° for about 16 hours
  7. dissolutionThe mixture was dissolved in aqueous ethanol
  8. additiontreated with activated charcoal
  9. temperaturechilled for two days at about 5°
  10. filtrationThe separated solid was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-870ad827e3374148a6866bae3f8e0adf
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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