Dimethylformamide dimethyl acetal → N'-[4-cyano-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-N,N-dimethylimidoformamide

HRID 550411

Reaction equation

HRID 550411 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([O:7][CH2:8][CH2:9][OH:10])[C:3]=1[C:11]#[N:12].CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>C(#N)C>[C:11]([C:3]1[C:4]([O:7][CH2:8][CH2:9][OH:10])=[N:5][NH:6][C:2]=1[N:1]=[CH:15][N:16]([CH3:18])[CH3:17])#[N:12]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 162289095-amino-3-(2-hydroxyethoxy)-1H-pyrazole-4-carbonitrile

Product 1

HCID 67020529N'-[4-cyano-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-N,N-dimethylimidoformamideYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

5-amino-3-(2-hydroxyethoxy)-1H-pyrazole-4-carbonitrile (prepared as described in Middleton, W. J., J. Am. Chem. Soc., 1958, 80, 2829/3.5 g, 20.8 mmol) and dimethylformamide dimethylacetal (4.15 ml, 31.3 mmol) were dissolved in acetonitrile (30 ml) and the mixture was stirred at 60° C. for 1 hour. The solvent was then removed under vacuum and the residue triturated in diethyl ether to provide a white solid, which was filtered and dried under vacuum to give N′-[4-cyano-3-(2-hydroxyethoxy)-1H-pyrazol-5-yl]-N,N-dimethylimidoformamide (4.45 g, 96%); NMR Spectrum: 2.95 (s, 3H), 3.06 (s, 3H), 3.67 (t, 2H), 4.12 (t, 2H) 8.09 (s, 1H); Mass Spectrum: 238 (MH+).

Workup

  1. customThe solvent was then removed under vacuum
  2. customthe residue triturated in diethyl ether
  3. customto provide a white solid, which
  4. filtrationwas filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-c914f53d718d4c129c9263204de8b7f5
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Linked notes

Loading…