Oxalyl chloride → Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate
Reaction equation
[ClH:1].[CH2:2]([O:9][C:10](=[O:17])[CH2:11][NH:12][CH:13]([C:15]#[N:16])[CH3:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:18](Cl)(=[O:22])[C:19]([Cl:21])=O>C1(C)C=CC=CC=1>[Cl:1][C:15]1[N:16]=[C:19]([Cl:21])[C:18](=[O:22])[N:12]([CH2:11][C:10]([O:9][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:17])[C:13]=1[CH3:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A suspension of benzyl-2-[(1-cyanoethyl)amino]acetate hydrochloride (preparation 16) (17.8 g, 69.88 mmol) in toluene (120 ml) was treated cautiously with oxalyl chloride (24.38 ml). Once effervescence had ceased the reaction was heated at 100° C. (24 hr). The reaction was cooled, solvent evaporated to dryness and the resultant crude product purified by chromatography (SiO2, gradient elution with 70:30 pentane:ethyl acetate; 50:50 pentane:ethyl acetate; 30:70 pentane:ethyl acetate; 100% ethyl acetate). Chromatography again, (SiO2, eluting with 100% CH2Cl2) gave the desired product as an off-white solid (9.40 g, 41%). 1H NMR (CD3OD) δ 2.35 (s, 3H), 4.90 (s, 2H), 5.25 (s, 2H), 7.40 (m, 5H).
Workup
- temperatureThe reaction was cooled
- customsolvent evaporated to dryness
- customthe resultant crude product purified by chromatography (SiO2, gradient elution with 70:30 pentane:ethyl acetate; 50:50 pentane:ethyl acetate; 30:70 pentane:ethyl acetate; 100% ethyl acetate)
- washChromatography again, (SiO2, eluting with 100% CH2Cl2)
Sources & evidence
- ORD record
- ord-01c05ba3ba1a4abc937e4f65a22905d7
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06180627B2
Reaction notes
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