Methanol → Tyclopyrazoflor

HRID 705490Notes

Reaction equation

Cl[CH2:2][CH2:3][C:4]([N:6]([C:9]1[C:10]([Cl:20])=[N:11][N:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:13]=1)[CH2:7][CH3:8])=[O:5].CO.[OH-].[K+].[F:25][C:26]([F:31])([F:30])[CH2:27][CH2:28][SH:29]>O.C(OCC)(=O)C>[Cl:20][C:10]1[C:9]([N:6]([CH2:7][CH3:8])[C:4](=[O:5])[CH2:3][CH2:2][S:29][CH2:28][CH2:27][C:26]([F:31])([F:30])[F:25])=[CH:13][N:12]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[N:11]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A 100 mL, 3-neck round bottom flask was charged with 3-chloro-N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethylpropanamide (500 mg, 1.60 mmol) and methanol (10 mL), potassium hydroxide (107 mg, 1.92 mmol) was added, followed by 3,3,3-trifluoro-propane-1-thiol (249 mg, 1.92 mmol) The mixture was heated at 50° C. for 4 hours, at which point thin layer chromatography analysis [Eluent: ethyl acetate] indicated the reaction was complete to give exclusively a new product. The reaction mixture was cooled to 20° C. and diluted with water (20 mL) and ethyl acetate (20 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (20 mL). The organics were dried over sodium sulfate (Na2SO4) and concentrated to dryness to afford a light yellow oil, which solidified upon standing to give a light yellow solid (650 mg, quantitative).

Workup

additionwas added
customto give exclusively a new product
customThe layers were separated
extractionthe aqueous layer was extracted with ethyl acetate (20 mL)
dry with materialThe organics were dried over sodium sulfate (Na2SO4)
concentrationconcentrated to dryness
customto afford a light yellow oil, which
customto give a light yellow solid (650 mg, quantitative)

Sources & evidence

ORD record: ord-86422289bc144ce18ee75182891fa2d9
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174962B2

Reaction notes

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