Pyridine → HCID 178428867, compound

HRID 1254935Notes

Reaction equation

[CH3:1][C:2]1[C:10]([S:11]([CH3:13])=[O:12])=[C:9]([C:14]([F:17])([F:16])[F:15])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[OH:18][C:19]1[N:20]([CH3:24])[N:21]=[CH:22][CH:23]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>C(OCC)(=O)C.O>[OH:18][C:19]1[N:20]([CH3:24])[N:21]=[CH:22][C:23]=1[C:4]([C:3]1[CH:7]=[CH:8][C:9]([C:14]([F:17])([F:16])[F:15])=[C:10]([S:11]([CH3:13])=[O:12])[C:2]=1[CH3:1])=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

3.0 g of 2-methyl-3-methylsulfinyl-4-trifluoromethylbenzoic acid and 1.25 g of 3-hydroxy-2-methylpyrazole are suspended in 20 ml of ethyl acetate and 4.8 g of pyridine under an inert atmosphere and cooled to −25° C. with stirring. 1.51 g of thionyl chloride are then slowly added dropwise such that the temperature always remains below −20° C. Following the complete addition of the thionyl chloride, the mixture is stirred for a further 20 minutes. 40 μl of cold water, 10 ml of ethyl acetate and a further 10 ml of water are added, and the mixture is heated to 0° C. After separating the organic phase from the aqueous phase, the aqueous phase is extracted twice with 5 ml of ethyl acetate in each case. The combined organic phases are dried, giving 3.69 g of (5-hydroxy-1-methyl-1H-pyrazol-4-yl)[2-methyl-3-(methylsulfinyl)-4-(trifluoromethyl)phenyl]methanone (90.7% yield).

Workup

stirringthe mixture is stirred for a further 20 minutes
customAfter separating the organic phase from the aqueous phase
extractionthe aqueous phase is extracted twice with 5 ml of ethyl acetate in each case
customThe combined organic phases are dried

Sources & evidence

ORD record: ord-24014dcef42f4290bacbafe7abafe8da
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455657B2

Reaction notes

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