2-(Ethoxymethylene)propanedinitrile → 5-Amino-4-cyano-1-(2,2-diethoxyethyl)pyrazole

HRID 1463991Notes

Reaction equation

HRID 1463991 reaction equation
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[CH2:5][NH:6][NH2:7])[CH3:2].C(O[CH:14]=[C:15]([C:18]#[N:19])[C:16]#[N:17])C>C(O)C>[NH2:19][C:18]1[N:6]([CH2:5][CH:4]([O:8][CH2:9][CH3:10])[O:3][CH2:1][CH3:2])[N:7]=[CH:14][C:15]=1[C:16]#[N:17]

Participants

4

Reactant 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 322952(2,2-Diethoxyethyl)hydrazine

Product 1

HCID 3402435-Amino-4-cyano-1-(2,2-diethoxyethyl)pyrazoleYield 30.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of hydrazinoacetaldehyde diethyl acetal (52.6 g) in ethanol (110 ml) was added dropwise a solution of ethoxymethylenemalononitrile (41.5 g) in ethanol (420 ml) at room temperature. The mixture was stirred at ambient temperature for 24 hours. The reaction mixture was evaporated in vacuo. To the residue was added diethyl ether (400 ml) and the resultant precipitate was filtered off. The filtrate was subjected to column chromatography on silica gel using a mixture of ethyl acetate and hexane (2:3) as an eluent. Fractions containing the object compound were combined and evaporated to give 5-amino-4-cyano-1-(2,2-diethoxyethyl)pyrazole (23.0 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionTo the residue was added diethyl ether (400 ml)
  3. filtrationthe resultant precipitate was filtered off
  4. additiona mixture of ethyl acetate and hexane (2:3) as an eluent
  5. additionFractions containing the object compound
  6. customevaporated

Sources & evidence

ORD record
ord-cd08060c5a034259aca58f73dbb16c0c
Source dataset
uspto-grants-1994_04
Patent number
US05302712

Reaction notes

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