Water → HCID 10665314, compound

HRID 565818Notes

Reaction equation

[CH:1]1([S:4][C:5]([F:18])([F:17])[C:6]2([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=3[F:16])[CH2:8][O:7]2)[CH2:3][CH2:2]1.[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH:1]1([S:4][C:5]([F:18])([F:17])[C:6]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])([OH:7])[CH2:8][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 2-[(cyclopropylthio) (difluoro)-methyl]-2-(2,4-difluorophenyl)oxirane (5.0 g, 0.017 mol) in DMSO (70 ml), 1,2,4-triazole (3.48 g, 0.05 mol) and potassium carbonate (6.95 g, 0.05 mol) were added, followed by stirring at 55° C. for 1.5 hours. After the completion of the reaction, water was added to the reaction mixture. The resulting mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated saline and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue so obtained was crystallized from isopropyl ether—ethyl acetate, whereby 1-(cyclopropylthio)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-1,2,4-triazol-1-yl)-2-propanol (2.35 g, yield: 32%) was obtained as colorless crystals.

Workup

additionwas added to the reaction mixture
extractionThe resulting mixture was extracted with ethyl acetate
washThe extract was washed successively with water and saturated saline
dry with materialdried over magnesium sulfate
distillationThe solvent was then distilled off under reduced pressure
customThe residue so obtained
customwas crystallized from isopropyl ether—ethyl acetate

Sources & evidence

ORD record: ord-fea0167754754b4883b31a15c52c4ba0
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172266B2

Reaction notes

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