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

HRID 878396Notes

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 per cent).

Workup

concentrationSubsequently, the solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-431d7eaba51e46cc998d3a726c11d113
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987460B2

Reaction notes

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