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

HRID 2044028Notes

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]>CC#N>[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: 70 °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 CH3CN and the solution was heated to 70° C. (26 g, 0.22 mol) of SOCl2 (0.12 mol) was slowly added dropwise at this temperature. The mixture was after-stirred for 1 hour at 70° C. and concentrated by evaporation in vacuo. This gave 27.6 g (92%) of the product as viscous oil with a purity of 95%.

Workup

additionwas slowly added dropwise at this temperature
concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record: ord-581b101e1f3840039608b5f8ac5bc900
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586753B2

Reaction notes

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