Chlorobenzene → 1-(4-methoxybenzyl)-3,5-dichloropyrazine-2(1H)-one

HRID 1752591Notes

Reaction equation

HRID 1752591 reaction equation
[C:1]([Cl:6])(=O)[C:2](Cl)=[O:3].[CH3:7][O:8][C:9]1[CH:19]=[CH:18][C:12]([CH2:13][NH:14][CH2:15][C:16]#[N:17])=[CH:11][CH:10]=1.[Cl:20]C1C=CC=CC=1>>[Cl:6][C:1]1[C:2](=[O:3])[N:14]([CH2:13][C:12]2[CH:18]=[CH:19][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)[CH:15]=[C:16]([Cl:20])[N:17]=1

Participants

4

Reactant 3

HCID 7964ChlorobenzeneHCID 65578Oxalyl chlorideHCID 99897602-((4-Methoxybenzyl)amino)acetonitrile

Product 1

HCID 154984631-(4-methoxybenzyl)-3,5-dichloropyrazine-2(1H)-oneYield 27.6%

Conditions

Temperature
90 °C

Procedure

Oxalyl chloride (17.5 ml, 200 mmol) was added dropwise via a dropping funnel to a mixture of compound (7) (8.5 g, 48.2 mmol) in chlorobenzene (60 ml). The reaction was heated at about 90° C. for about 16 h. The solvent was removed. The resulting mixture was deposited onto silica gel and loaded onto a silica gel column and eluted with Hex/EtOAc (10:1) to afford 3,5-dichloro-1-(4-methoxybenzyl)pyrazin-2(1H)-one (4.0 g, 13.33 mmol, 27.6% yield).

Workup

  1. customThe solvent was removed
  2. washeluted with Hex/EtOAc (10:1)

Sources & evidence

ORD record
ord-d1e363b693b9486db13c1212ecc1d64a
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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