Oxalyl chloride → 1-benzyl-3,5-dichloropyrazin-2(1H)-one

HRID 218538Notes

Reaction equation

HRID 218538 reaction equation
[C:1]([Cl:6])(=O)[C:2](Cl)=[O:3].[CH:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][CH2:15][C:16]#[N:17])=[CH:9][CH:8]=1.[ClH:18]>ClC1C=CC=CC=1Cl>[CH2:13]([N:14]1[CH:15]=[C:16]([Cl:18])[N:17]=[C:1]([Cl:6])[C:2]1=[O:3])[C:10]1[CH:11]=[CH:12][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 125715482-(Benzylamino)acetonitrile hydrochloride

Product 1

HCID 112998051-benzyl-3,5-dichloropyrazin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 92 g (725 mmol) of oxalyl chloride in 188 ml of 1,2-dichlorobenzene are added 26.5 g (145 mmol) of N-benzylaminoacetonitrile. The solution is heated to 60° C. for 20 min and to 90° C. for 6 h. It is allowed to cool and left at this temperature for 15 h. The solvent is removed under reduced pressure and the residue is eluted with silica gel and with a gradient from cyclohexane to 5:1 cyclohexane/ethyl acetate. The product fractions are combined and concentrated to dryness under reduced pressure. The residue is crystallized from diethyl ether. This affords 22 g (60% of theory) of the desired compound.

Workup

  1. temperatureto cool
  2. customThe solvent is removed under reduced pressure
  3. washthe residue is eluted with silica gel and with a gradient from cyclohexane to 5:1 cyclohexane/ethyl acetate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-51f59ec8e16f44ef91c2dc3c75fa50ba
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Reaction notes

Loading…