Malononitrile → HCID 18629257, compound

HRID 1066755Notes

Reaction equation

HRID 1066755 reaction equation
Cl.[CH3:2][CH2:3][CH:4]([NH:7][NH2:8])[CH2:5][CH3:6].[C:9](#[N:13])[CH2:10][C:11]#[N:12].[CH2:14](N(CC)CC)[CH3:15]>CO>[NH2:12][C:11]1[N:7]([CH:4]([CH2:5][CH3:6])[CH2:3][CH3:2])[N:8]=[C:14]([CH3:15])[C:10]=1[C:9]#[N:13]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8471TriethylamineHCID 717572031-(pentan-3-yl)hydrazine hydrochloride

Product 1

HCID 18629257HCID 18629257, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

11.9 g of 3-pentylhydrazine hydrochloride (Part A), 11.7 g of 1-ethoxyethylidine malononitrile and 26.0 g of triethylamine were dissolved in 100 mL of methanol and refluxed for a period of 20 h. The solvent was stripped in vacuo and partitioned the residue with 100 mL each of water and ethyl acetate and extracted the aqueous layer with 2*50 mL of ethyl acetate. The combined organic extracts were washed with brine, dried and stripped in vacuo to afford 16.8 g of brown oil. The oil was purified by flash column chromatography (1:100 MeOH/dichloromethane eluent) to afford 11.7 g (71%) of desired pyrazole derivative as a white crystalline solid (mp. 117-118° C.). Anal. calcd. for C10H16N4: C, 62.47; H, 8.40; N, 29.14. Found: C, 62.17; H, 8.39; N, 29.18.

Workup

  1. temperaturerefluxed for a period of 20 h
  2. custompartitioned the residue with 100 mL each of water and ethyl acetate
  3. extractionextracted the aqueous layer with 2*50 mL of ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. customdried

Sources & evidence

ORD record
ord-b5052a6722e649ec9985f5fd6a262eef
Source dataset
uspto-grants-2001_06
Patent number
US06245769B1

Reaction notes

Loading…