Malononitrile → 2-Amino-4,5-diphenyl-3-furonitrile

HRID 2189020Notes

Reaction equation

HRID 2189020 reaction equation
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)O)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](#[N:21])[CH2:18][C:19]#[N:20].C(N(CC)CC)C>CN(C=O)C>[NH2:21][C:17]1[O:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:18]=1[C:19]#[N:20]

Participants

5

Reactant 3

HCID 8010Malononitrile2×HCID 8400BenzoinHCID 8471Triethylamine

Product 1

HCID 3896992-Amino-4,5-diphenyl-3-furonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir 100 g (470 mmol) of benzoin, 62.25 g (940 mmol) of malononitrile and 47.68 g (470 mmol) of triethylamine at RT in 1345 ml of DMF overnight. Add a further 41 g (620 mmol) of malononitrile and stir the mixture at RT for another 24 h. Then add ethyl acetate and water and extract the aqueous phase twice with ethyl acetate. Dry the combined organic phases over magnesium sulphate and concentrate them under reduced pressure. After column chromatography on silica gel (eluent: dichloromethane→dichloromethane/methanol 98:2), 120 g (97.9% of theory) of the title compound are obtained as yellowish solid.

Workup

  1. extractionThen add ethyl acetate and water and extract the aqueous phase twice with ethyl acetate
  2. dry with materialDry the combined organic phases over magnesium sulphate
  3. concentrationconcentrate them under reduced pressure

Sources & evidence

ORD record
ord-6e1371b2ebe9463f8489e9a7f8c6c317
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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