Thionyl Chloride → Methyl 3-(chloromethyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate

HRID 1515372Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N:8]2[C:12](O)([C:13]([O:15][CH3:16])=[O:14])[CH2:11][C:10]([CH2:18]O)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.O=S(Cl)[Cl:22]>C(Cl)Cl>[Cl:22][CH2:18][C:10]1[CH:11]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[N:8]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[N:9]=1

Participants

Conditions

Temperature: 5 °C

Procedure

Methyl 1-(3-chloropyridin-2-yl)-5-hydroxy-3-(hydroxymethyl)-4,5-dihydro-1H-pyrazole-5-carboxylate (28.5 g, 0.1 mol) was dissolved in 100 ml of CH2Cl2 and the solution was cooled to 5° C. SOCl2 (0.12 mol) in 30 ml of CH2Cl2 was slowly added dropwise at this temperature. The mixture was after-stirred for 4 hours at RT and concentrated by evaporation in vacuo. The product was purified by column chromography on SiO2 (eluent hexane/ethyl acetate). Oil.

Workup

concentrationconcentrated by evaporation in vacuo
customThe product was purified by column chromography on SiO2 (eluent hexane/ethyl acetate)

Sources & evidence

ORD record: ord-b1ef5ff4b3974434a41ac680da1ce14a
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222435B2

Reaction notes

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