Phenacyl bromide → 2-Amino-5-phenylfuran-3-carbonitrile

HRID 1926865Notes

Reaction equation

HRID 1926865 reaction equation
C(NCC)C.Br[CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9].[C:16](#[N:20])[CH2:17][C:18]#[N:19]>CN(C=O)C>[NH2:20][C:16]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][C:17]=1[C:18]#[N:19]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 8010MalononitrileHCID 8021Diethylamine

Product 1

HCID 6939612-Amino-5-phenylfuran-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add 68.6 ml (663 mmol) diethylamine dropwise to a mixture of 60.0 g (301 mmol) bromoacetophenone and 25.89 g (391.86 mmol) malononitrile in 130 ml DMF at RT (cooling is required to maintain the temperature). Towards the end of addition, remove the cooling, stir the mixture for 1 h at RT and then add water to 385 ml. Dilute with a further 125 ml water and stir for 20 min at RT. Filter off the precipitated solids with suction, wash twice with 125 ml water each time, dry under suction and wash with petroleum ether. Dry the residue at high vacuum. 33.3 g (50.1% of theor.) of the target compound is obtained as yellowish-brown crystals.

Workup

  1. temperaturecooling
  2. temperatureto maintain the temperature)
  3. additionTowards the end of addition
  4. customremove the cooling
  5. additionDilute with a further 125 ml water
  6. stirringstir for 20 min at RT
  7. filtrationFilter off the precipitated solids with suction
  8. washwash twice with 125 ml water each time
  9. customdry under suction
  10. washwash with petroleum ether
  11. customDry the residue at high vacuum
  12. custom33.3 g (50.1% of theor.) of the target compound is obtained as yellowish-brown crystals

Sources & evidence

ORD record
ord-799545910e3643d2b6cbd60062af3c0c
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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