Water → 2-Amino-4-(4-ethylphenyl)-5-phenyl-3-furancarbonitrile

HRID 1926884Notes

Reaction equation

HRID 1926884 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH:10]([OH:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)[CH3:2].[C:19](#[N:23])[CH2:20][C:21]#[N:22].C(NCC)C.O>CN(C=O)C>[NH2:23][C:19]1[O:17][C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[C:20]=1[C:21]#[N:22]

Participants

6

Reactant 4

HCID 962Water3×HCID 8010MalononitrileHCID 8021DiethylamineHCID 53691566HCID 53691566, compound

Product 1

HCID 580168122-Amino-4-(4-ethylphenyl)-5-phenyl-3-furancarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cool a mixture of 145 g (603 mmol) 1-(4-ethylphenyl)-2-hydroxy-2-phenylethanone and 51.8 g (784.4 mmol) malononitrile in 2.23 litres DMF to 0° C. and add 53.7 ml (518 mmol) diethylamine, with cooling. After 1 h, heat the reaction mixture to RT and stir for a further 4 h, before adding 1.5 litre water. After 30 min, pour off a large proportion of the water and replace with 750 ml of fresh water. Stir the mixture vigorously, before decanting from the sticky organic residue. Dissolve the residue in ethyl acetate, dry, and concentrate under vacuum, until the product begins to crystallize. Add 450 ml diisopropyl ether, stir and then leave to stand overnight. Filter off the crystalline precipitate with suction, wash twice with 50 ml diisopropyl ether and dry under vacuum. 98.5 g (56.6% of theor.) of the target product is obtained.

Workup

  1. temperatureCool
  2. temperaturewith cooling
  3. waitAfter 30 min
  4. stirringStir the mixture vigorously
  5. custombefore decanting from the sticky organic residue
  6. dissolutionDissolve the residue in ethyl acetate
  7. customdry
  8. concentrationconcentrate under vacuum, until the product
  9. customto crystallize
  10. additionAdd 450 ml diisopropyl ether
  11. stirringstir
  12. customleave
  13. waitto stand overnight
  14. filtrationFilter off the crystalline precipitate with suction
  15. washwash twice with 50 ml diisopropyl ether
  16. customdry under vacuum
  17. custom98.5 g (56.6% of theor.) of the target product is obtained

Sources & evidence

ORD record
ord-e8fc03077b3e40978b4ce3785b4bfa1e
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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