Dimethylformamide → HCID 689304, compound

HRID 1355821Notes

Reaction equation

HRID 1355821 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:20])[C:15]1OC=C[CH:16]=1.[CH3:21][N:22](C=O)C>C(O)C.C(N(CC)CC)C>[NH2:13][C:11]1[S:12][C:21]([NH2:22])=[C:2]([C:1]#[N:7])[CH:4]([C:5]2[O:20][CH:14]=[CH:15][CH:16]=2)[C:10]=1[C:8]#[N:9]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7362FurfuralHCID 14162772-CyanoethanethioamideHCID 212535622-Hydroxybutanedinitrile

Product 1

HCID 689304HCID 689304, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 702EthanolSolvent

Procedure

Following an adaptation of the method of Elghandour et al. (Ind. J. Chem. 1997, B36, 79), to a stirred solution of 3.98 g (60.3 mmol) malonitrile, 6.04 g (60.3 mmol) cyanothioacetamide and 5.0 ml (60.3 mmol) furfural in 100 ml ethanol and 5 ml DMF at 0° C. was added dropwise 0.4 ml (3.0 mmol) triethylamine and stirring was continued at 0° C. for 2 hours. The resulting crystals were collected by filtration and washed with ice-cold ether to afford 10.4 g (71%) 2,6-diamino-4-furan-2-yl-4H-thiopyran-3,5-dicarbonitrile as a white crystalline solid. EI-MS m/e (%): 244 (M+, 100), 211 ([M—SH]+, 64), 60 (50).

Workup

  1. filtrationThe resulting crystals were collected by filtration
  2. washwashed with ice-cold ether

Sources & evidence

ORD record
ord-ef82cd27590742e7bbd1ca6f721c9acd
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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