Hydrochloric Acid → HCID 89858775, compound

HRID 919164Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:10]([S:11]([C:13]([F:16])([F:15])[F:14])=[O:12])=[C:9]([CH3:17])[N:8]([C:18]2[C:23]([F:24])=[CH:22][C:21]([C:25]([F:28])([F:27])[F:26])=[CH:20][C:19]=2[Cl:29])[N:7]=1)=[O:5])C.[OH-].[Li+].Cl>C(O)(C)C.O>[Cl:29][C:19]1[CH:20]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:23]([F:24])[C:18]=1[N:8]1[C:9]([CH3:17])=[C:10]([S:11]([C:13]([F:14])([F:15])[F:16])=[O:12])[C:6]([C:4]([OH:5])=[O:3])=[N:7]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(2-Chloro-6-fluoro-4-trifluoromethyl-phenyl)-5-methyl-4-trifluoromethanesulfinyl-1H-pyrazole-3-carboxylic acid ethyl ester (1.2 g, 2.6 mmol) in isopropanol (10 mL) and water (2.5 mL) was added lithium hydroxide (0.2 g, 8.4 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 2 h. To the reaction mixture was added aqueous hydrochloric acid (37 wt %, 0.9 mL) and water (7 mL). The resulting mixture was extracted with EtOAc. The organic layer was washed with water, dried (MgSO4) and concentrated under reduced pressure to give 1-(2-Chloro-6-fluoro-4-trifluoromethyl-phenyl)-5-methyl-4-trifluoromethanesulfinyl-1H-pyrazole-3-carboxylic acid as an off-white solid (1.1 g). This material was used without purification for the next step. 1H NMR (400 MHz, CDCl3) δ ppm 2.52 (s, 3H), 7.56 (dd, J=8.3, 1.5 Hz, 1H), 7.73 (s, 1H). 19F NMR (376 MHz, CDCl3) δ ppm −113.4 (d, J=8.6 Hz, 0.5F), −112.9 (d, J=7.9 Hz, 0.5F), −73.9 (s, 1.5F), −73.7 (s, 1.5F), −63.8 (s, 3F).

Workup

extractionThe resulting mixture was extracted with EtOAc
washThe organic layer was washed with water
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-1288bff474c44600a70853f09e09da05
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273007B2

Reaction notes

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