1,2-Dichlorobenzene → Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate

HRID 1016255

Reaction equation

HRID 1016255 reaction equation
[C:1]([Cl:6])(=O)[C:2](Cl)=[O:3].[ClH:7].C([N:15]([CH:20]([C:22]#[N:23])[CH3:21])CC(O)=O)C1C=CC=CC=1.[C:24]([O:27][CH2:28][CH3:29])(=[O:26])[CH3:25].Cl[C:31]1[CH:36]=[CH:35]C=[CH:33][C:32]=1Cl>CCCCCC>[CH2:28]([O:27][C:24]([CH2:25][N:15]1[C:20]([CH3:21])=[C:22]([Cl:7])[N:23]=[C:1]([Cl:6])[C:2]1=[O:3])=[O:26])[C:29]1[CH:35]=[CH:36][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 72391,2-DichlorobenzeneHCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 68560147Benzyl-N-(1-cyanoethyl)glycine hydrochloride

Product 1

HCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetateYield 55%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of oxalyl chloride (5.3 mL, 60 mmol) and benzyl-N-(1-cyanoethyl)glycine hydrochloride (3.82 g, 15 mmol), as prepared in the preceding step, in 1,2-dichlorobenzene (30 mL) was heated to 100° C. overnight. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography to give a solid. 10% Ethyl acetate in hexane (100 mL) was added and the solid was collected to give the title compound as an orange crystalline solid (2.7 g, 55%). 1H NMR (CDCl3) δ 7.38 (m, 5H), 5.24 (s, 2H), 4.89 (s, 2H), 2.34 (s,3H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography
  3. customto give a solid
  4. customthe solid was collected

Sources & evidence

ORD record
ord-bdad4dda17044672b6408bb9714041a7
Source dataset
uspto-grants-2002_11
Patent number
US06476016B2

Linked notes

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