Benzyl Bromide → HCID 68836020, compound

HRID 747747Notes

Reaction equation

HRID 747747 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][CH:24]=1)[O:8][CH2:9][CH2:10][NH:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=1)#[N:4].[H][H].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O>[C:3]([C:5]1[CH:6]=[C:7]([CH:22]=[CH:23][CH:24]=1)[O:8][CH2:9][CH2:10][N:11]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=1)#[N:4]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 11066232N-[2-(3-cyanophenoxy)ethyl]-4-cyanobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 68836020HCID 68836020, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

28 mg (0.7 mmol) of sodium hydride (oily, 60%) was stirred in dimethylformamide under cooling with ice. A solution of 200 mg (0.69 mmol) of N-[2-(3-cyanophenoxy)ethyl]-4-cyanobenzamide in a small amount of dimethylformamide was added thereto. After the completion of the generation of hydrogen, 257 mg (1.5 mmol) of benzyl bromide was added to the mixture, and they were stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure. 1N aqueous hydrogen chloride solution was added to the residue. The same procedure for the isolation as that of step 1 in Example 1 was repeated with ethyl acetate as the extractant to obtain the title compound.

Workup

  1. temperatureunder cooling with ice
  2. customThe solvent was evaporated under reduced pressure
  3. addition1N aqueous hydrogen chloride solution was added to the residue

Sources & evidence

ORD record
ord-68a4618e5a1a4f04bfb74452ca7ecf19
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

Loading…