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

HRID 1057405Notes

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

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 (20-30% ethyl acetate in hexane) 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 (300 MHz, CDCl3) δ 7.38 (m, 5H), 5.24 (s, 2H), 4.89 (s, 2H), 2.34 (S, 3H).

Workup

customThe solvent was evaporated in vacuo
customthe residue was purified by flash column chromatography (20-30% ethyl acetate in hexane)
customto give a solid
customthe solid was collected

Sources & evidence

ORD record: ord-1d1ebf3e543c46028fe8b12b982e5d4e
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06514978B2

Reaction notes

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