Dimethylformamide → 2-{4-[(3,5-Dichloropyridin-2-yl)oxy]phenoxy}propanoyl chloride

HRID 249200Notes

Reaction equation

S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:7]([O:13][C:14]2[CH:25]=[CH:24][C:17]([O:18][CH:19]([CH3:23])[C:20](O)=[O:21])=[CH:16][CH:15]=2)=[N:8][CH:9]=[C:10]([Cl:12])[CH:11]=1.CN(C)C=O>C(Cl)(Cl)Cl>[Cl:5][C:6]1[C:7]([O:13][C:14]2[CH:25]=[CH:24][C:17]([O:18][CH:19]([CH3:23])[C:20]([Cl:3])=[O:21])=[CH:16][CH:15]=2)=[N:8][CH:9]=[C:10]([Cl:12])[CH:11]=1

Participants

Conditions

Temperature: 63 °C

Procedure

Thionyl chloride (18.8 mL, 257.1 mmol) is added dropwise to a mixture of 2-{p-[(3,5-dichloro-2-pyridyl)oxy]phenoxy}propionic acid (21.1 g, 64.3 mmol) in chloroform (220 mL). When the addition is complete, dimethylformamide (1.5 mL) is added and the reaction mixture is stirred for 21 hours at 63° C., concentrated in vacuo and chased with chloroform to obtain the title product as a yellow syrup which is identified by 1H NMR spectral analysis.

Workup

additionWhen the addition
concentrationconcentrated in vacuo and chased with chloroform

Sources & evidence

ORD record: ord-9c29c95b3e804780a4b286297116dea5
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05213606

Reaction notes

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