Dimethylformamide → 4-(2-oxo-2-phenylethyl)benzonitrile

HRID 1608287Notes

Reaction equation

HRID 1608287 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].CN.[H][H].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN(C=[O:29])C>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:29])=[CH:5][CH:4]=1)#[N:2]

Participants

8

Reactant 6

HCID 6228Dimethylformamide2×HCID 6329MethylamineHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 2660704-(2-oxo-2-phenylethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 2-(4-cyanophenyl)-1-phenylethanone was synthesized from 4-cyanobenzyl bromide and ω-cyano-N,N-diethylbenzenemethanamine: 3.95 g (0.16 mol) of sodium hydride was suspended in 80 mL of DMF under nitrogen and 29.9 g (0.16 mol) of the methanamine in 20 mL of DMF was added dropwise. When evolution of hydrogen had ceased, 31.2 g (0.16 mol) of the benzyl bromide in 30 mL of toluene was added and the reaction stirred 3 hr at room temperature. The reaction was stripped, 300 mL of 6N HCL was added and the suspension was stirred 4 hr, let sit 18 hr and extracted with chloroform. The chloroform extract was stripped, dissolved in ethyl acetate, and filtered through silica gel to remove a purple impurity. The ethyl acetate solution was stripped, the residue was triturated in ether and recrystallized from methanol to give 7.72 g of 2-(4-cyanophenyl)-1-phenylethanone, mp 113°-114° C.

Workup

  1. addition300 mL of 6N HCL was added
  2. stirringthe suspension was stirred 4 hr
  3. waitlet sit 18 hr
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. dissolutiondissolved in ethyl acetate
  7. filtrationfiltered through silica gel
  8. customto remove a purple impurity
  9. customthe residue was triturated in ether
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-1f0c6ab18f09479e90851b070215eafa
Source dataset
uspto-grants-1989_09
Patent number
US04870095

Reaction notes

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