Pyridine → HCID 178477618, compound

HRID 1254934Notes

Reaction equation

[CH3:1][C:2]1[C:10]([S:11]([CH2:13][CH3:14])=[O:12])=[C:9]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[OH:19][C:20]1[N:21]([CH3:25])[N:22]=[CH:23][CH:24]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>C(OCC)(=O)C.O>[CH2:13]([S:11]([C:10]1[C:2]([CH3:1])=[C:3]([C:4]([C:24]2[CH:23]=[N:22][N:21]([CH3:25])[C:20]=2[OH:19])=[O:6])[CH:7]=[CH:8][C:9]=1[S:15]([CH3:18])(=[O:17])=[O:16])=[O:12])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

305 mg of 2-methyl-3-ethylsulfinyl-4-methylsulfonylbenzoic acid and 106 mg of 3-hydroxy-2-methylpyrazole are suspended in 2 ml of ethyl acetate and 407 mg of pyridine under an inert atmosphere and cooled to −25° C. with stirring. 129 mg 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. A further 27 mg of 3-hydroxy-2-methylpyrazole are added, and 42 mg of thionyl chloride are slowly added dropwise such that the temperature always remains below −25° C. 4 μl of cold water are then added and the mixture is warmed 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 370 mg of [3-(ethylsulfinyl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone (91% 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-eaa9469cb90f4e17b4c18ef10f4e1df6
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455657B2

Reaction notes

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