Oxalyl chloride → N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolane-4-ylidene)-N-methoxy-acetamide

HRID 2214678Notes

Reaction equation

[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8]([OH:10])=O)[C:4](=[O:11])[O:3]1.C(Cl)(=O)C(Cl)=O.[Cl:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:23][NH:24][O:25][CH3:26]>C1C=CC=CC=1.ClCCl.N1C=CC=CC=1.Cl>[Cl:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:23][N:24]([O:25][CH3:26])[C:8](=[O:10])[CH:7]=[C:5]1[C:4](=[O:11])[O:3][C:2]([CH3:1])([CH3:12])[O:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetic acid (4.37 g, 25.4 mmol) in benzene (30 mL) was refluxed for 1 h with oxalyl chloride (15 mL). The resulting solution was cooled and concentrated. The residue was dissolved in dichloromethane (30 mL) and cooled to 0° C. and N-(3,4-dichloro-benzyl)-O-methyl-hydroxylamine (5.3 g, 22 mmol) in dichloromethane (30 mL) and pyridine (18 mL) was added dropwise. The resulting mixture was stirred at room temp for 18 h. The mixture was diluted with 1N HCl and extracted with EtOAc. The organic phase was washed with 1N HCl, dried (sodium sulfate) and concentrated to give the title compound as a yellow solid (7.59 g, 83% yield). 1HNMR (300 MHz, CDCl3) δ: 7.44 (1H, s), 7.39 (2H, d, J=8.05 Hz), 7.19 (2H, d, J=8.05 Hz), 6.37 (1H, s), 4.75 (2H, s), 3.70 (3H, s), 1.74 (6H, s).

Workup

temperatureThe resulting solution was cooled
concentrationconcentrated
dissolutionThe residue was dissolved in dichloromethane (30 mL)
extractionextracted with EtOAc
washThe organic phase was washed with 1N HCl
dry with materialdried (sodium sulfate)
concentrationconcentrated

Sources & evidence

ORD record: ord-d27a9d54960b438587b251db3a54a29a
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109186B2

Reaction notes

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