Diphenylacetonitrile → HCID 12356700, compound

HRID 1741767Notes

Reaction equation

HRID 1741767 reaction equation
[H-].[Na+].[C:3]1([CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].Cl[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C)C=O>[C:23]([CH2:22][CH2:21][C:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:10]#[N:11])([O:25][CH2:26][CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 6837DiphenylacetonitrileHCID 24758Sodium hydrideHCID 69341Ethyl 3-chloropropionateHCID 178418361HCID 178418361, compound

Product 1

HCID 12356700HCID 12356700, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (27 g of a 60% oil suspension) in 600 mL of dry dimethylformamide at room temperature was added over 1 hour a solution of diphenyl acetonitrile (130 g, o.67 mol) in 400 mL of DMF. the mixture was stirred until the evolution of hydrogen ceased, about 1 hour. Ethyl 3-chloropropionate (90 mL, 1 mol) was added dropwise over 1 hour and the resulting mixture was stirred for a further 1 hour, then it was partitioned between water and ether. The organic layer was washed with brine and dried. Concentration of the solvents afforded a residue which was vacuum distilled to give 4-carbethoxy-2,2-diphenylbutanenitrile (110 g).

Workup

  1. customit was partitioned between water and ether
  2. washThe organic layer was washed with brine
  3. customdried
  4. customConcentration of the solvents afforded a residue which
  5. distillationdistilled

Sources & evidence

ORD record
ord-e3935002e861484a9146ed8648e4a9b3
Source dataset
uspto-grants-1994_08
Patent number
US05334720

Reaction notes

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