Benzaldehyde → NSC678060

HRID 1355704Notes

Reaction equation

HRID 1355704 reaction equation
[C:1](#[N:7])[CH:2]([CH2:4][C:5]#N)O.[C:8]([CH2:10][C:11]([NH2:13])=[S:12])#[N:9].[CH:14](=O)[C:15]1C=C[CH:18]=[CH:17][CH:16]=1.[NH:22]1CCCC[CH2:23]1.Cl>C(O)C>[NH2:22][C:23]1[NH:13][C:11](=[S:12])[C:10]([C:8]#[N:9])=[C:4]([C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:2]=1[C:1]#[N:7]

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 8082PiperidineHCID 14162772-CyanoethanethioamideHCID 212535622-Hydroxybutanedinitrile

Product 1

HCID 780902NSC678060Yield 95.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the method of Elghandour et al. (Ind. J Chem. 1997, B36, 79), a stirred solution of 0.66 g (10 mmol) malonitrile, 1.0 g (10 mmol) cyanothioacetamide, 1.0 ml (10 mmol) benzaldehyde and 0.1 ml (1.0 mmol) piperidine in 50 ml ethanol was heated at reflux for 1.5 hours. The reaction mixture was then poured onto ice-water and acidified to pH 3 with 1M hydrochloric acid. The resulting crystals were collected by filtration. Chromatography (ethyl acetate) afforded 0.24 g (10%) 6-amino-4-phenyl-2-thioxo-1,2-dihydro-pyridine-3,5-dicarbonitrile as a yellow crystalline solid. EI-MS m/e (%): 252 (M+, 100), 251 ([M—H]+, 92).

Workup

  1. temperatureat reflux for 1.5 hours
  2. additionThe reaction mixture was then poured onto ice-water
  3. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-c7887f433b944d749a02c639a602dfa6
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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