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

HRID 524133Notes

Reaction equation

[ClH:1].[Cl:2][C:3]1[C:4]([N:9]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]([CH2:17]O)=[N:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.O=S(Cl)Cl.[CH3:23]O>C1(C)C=CC=CC=1>[Cl:1][CH2:17][C:11]1[CH:12]=[C:13]([C:14]([O:16][CH3:23])=[O:15])[N:9]([C:4]2[C:3]([Cl:2])=[CH:8][CH:7]=[CH:6][N:5]=2)[N:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1-(3-Chloropyridin-2-yl)-3-(hydroxymethyl)-1H-pyrazole-5-carboxylic acid hydrochloride (0.1 mol) was initially charged in 50 ml of toluene. SOCl2 was added in portions at 60° C., The mixture was heated at 70° C. for 3 h, in the course of which the precipitate went completely into the solution. Methanol (30 ml) was slowly added dropwise to the mixture and the solution was stirred at room temperature for one hour. Subsequently, the solution was concentrated under reduced pressure. This afforded 95% of the product with a purity of 96% (area percent).

Workup

concentrationSubsequently, the solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-5277eec1e70a4b1f9cff825d068608c4
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340526B2

Reaction notes

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