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

HRID 1811358Notes

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-ea57537e45b44a749213ce746d026c75
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362261B2

Reaction notes

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