2-Cyanoethanethioamide → 6-Amino-4-furan-2-yl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile

HRID 1356046Notes

Reaction equation

HRID 1356046 reaction equation
N[C:2]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)=[CH:3][C:4]#[N:5].[C:11]([CH2:13][C:14]([NH2:16])=[S:15])#[N:12]>O1CCOCC1>[NH2:5][C:4]1[NH:16][C:14](=[S:15])[C:13]([C:11]#[N:12])=[C:2]([C:6]2[O:7][CH:8]=[CH:9][CH:10]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 14162772-CyanoethanethioamideHCID 692835483-Amino-3-(2-furyl)acrylonitrile

Product 1

HCID 185073536-Amino-4-furan-2-yl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrileYield 17%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following the method of Elnagdi and Erian (Arch. Pharm. 1991, 324, 853-858), to a stirred solution of 5.00 g (37.3 mmol) (E or Z)-3-amino-3-furan-2-yl-acrylonitrile in 50 ml dioxane at room temperature was added 7.46 (74.5 mmol) 2-cyanothioacetamide and the reaction mixture heated at reflux for 72 hours. The reaction mixture was then concentrated in vacuo. Chromatography (ethyl acetate/hexane 1/1 then ethyl acetate) afforded 1.40 g (17%) 6-amino-4-furan-2-yl-2-thioxo-1,2-dihydro-pyridine-3-carbonitrile as an orange crystalline solid, ES-MS m/e (%): 218 (M+H+, 100), and 0.46 g (6%) 2,6-diamino-4-furan-2-yl-nicotinonitrile as an orange crystalline solid, ES-MS m/e (%): 201 (M+H+, 100).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 72 hours
  3. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-c5ad11e016534cbabfa4615dca5030cf
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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