3-Ethoxy-2-propenenitrile → HCID 18692770, compound

HRID 1870675Notes

Reaction equation

HRID 1870675 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:9]=[N:8][NH:7][C:6]=1[NH2:10])([O-:4])=[O:3].C(O[CH:14]=[CH:15][C:16]#[N:17])C>C(O)(=O)C>[ClH:1].[N+:2]([C:5]1[CH:9]=[N:8][N:7]2[C:16]([NH2:17])=[CH:15][CH:14]=[N:10][C:6]=12)([O-:4])=[O:3]

Participants

4

Reactant 2

HCID 436013-Ethoxy-2-propenenitrileHCID 22676973HCID 22676973, compound

Product 1

HCID 18692770HCID 18692770, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

50 g of 4-nitro-2H-pyrazole-3-ylamine hydrochloride (prepared according to H. Dorn and H. Dilcher, Liebigs Ann. Chem., 707, 141, 1967) 35 g of β-ethoxyacrylonitrile and 250 cc of acetic acid were introduced into a 500 cc three-necked round-bottomed flask fitted with a mechanical stirrer and equipped with a condenser and a thermometer. The medium was refluxed for 4h30'. The mixture was cooled to about 40° C. and the precipitate was then filtered off. This precipitate was taken up in 300 cc of ethyl ether with stirring. The precipitate was filtered off again, washed on the filter with 100 cc of ethyl ether and the product was dried under vacuum over phosphorus pentoxide. 61.3 g of 3-nitropyrazolo[1,5-a]pyrimidin-7-ylamine hydrochloride were obtained in the form of a yellow powder. (Yield=93%).

Workup

  1. customfitted with a mechanical stirrer
  2. customequipped with a condenser
  3. temperatureThe medium was refluxed for 4h30'
  4. filtrationthe precipitate was then filtered off
  5. filtrationThe precipitate was filtered off again
  6. washwashed on the
  7. filtrationfilter with 100 cc of ethyl ether
  8. dry with materialthe product was dried under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-7bd67c9cb7f84860b7562ab42464812c
Source dataset
uspto-grants-2000_08
Patent number
US06099593

Reaction notes

Loading…