Oxalyl chloride → 3,5-Dichloro-1-methyl-1,2-dihydropyrazin-2-one

HRID 1854807Notes

Reaction equation

HRID 1854807 reaction equation
[ClH:1].[CH3:2][NH:3][CH2:4][C:5]#[N:6].[C:7]([Cl:12])(=O)[C:8](Cl)=[O:9]>ClC1C=CC=CC=1Cl>[Cl:12][C:7]1[C:8](=[O:9])[N:3]([CH3:2])[CH:4]=[C:5]([Cl:1])[N:6]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 117641Acetonitrile, 2-(methylamino)-, hydrochloride (1:1)

Product 1

HCID 130629683,5-Dichloro-1-methyl-1,2-dihydropyrazin-2-oneYield 60.8%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
80 °C

Procedure

3.29 g (30.8 mmoles) of methylamino-acetonitrile hydrochloride is placed in the presence of 19.6 g (154 mmoles) of oxalyl chloride in 30 ml of 1,2-dichlorobenzene. The mixture is heated for 8 hours at 80° C. After concentrating the reaction medium to dryness, the residue obtained is purified by flash chromatography (Petroleum ether-CH2Cl2 gradient 100-0 to 0-100). 3.35 g of intermediate 4c is obtained in beige powder form (yield: 60%).

Workup

  1. concentrationAfter concentrating the reaction medium to dryness
  2. customthe residue obtained
  3. customis purified by flash chromatography (Petroleum ether-CH2Cl2 gradient 100-0 to 0-100)

Sources & evidence

ORD record
ord-fbeeb1286590426a8f7b14de02b2d71d
Source dataset
uspto-grants-2015_02
Patent number
US08962837B2

Reaction notes

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