Sodium Hydroxide → 1-{[2-(2,4-Difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole monomethanesulfonate

HRID 543202

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C:10](=[O:17])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1.[I-].[CH3:19][S+:20]([CH3:23])(C)=[O:21].[OH-:24].[Na+]>C1(C)C=CC=CC=1.CCCCCCCCCCCCCC[N+](C)(C)C>[CH3:23][S:20]([OH:17])(=[O:21])=[O:24].[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C:10]1([O:17][CH2:19]1)[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1

Participants

Conditions

Temperature: 0 °C

Procedure

2',4'-Difluoro-2-(1H-1,2,4-triazol-1-yl)acetophenone hydrochloride (59.6 g, 0.23M), trimethylsulphoxonium iodide (50.6 g, 0.23M) and cetrimide (2.1 g) were stirred in a mixture of toluene (370 ml) and 20% w/w aqueous sodium hydroxide at 60° for 3 hours. The toluene layer was separated and concentrated to 110 ml then diluted with ethyl acetate (150 ml). A solution of methanesulphonic acid (16.6 g, 0.172M) in ethyl acetate (20 ml) was added. More ethyl acetate (100 ml) was added and the mixture was stirred at 0° C. for one hour then filtration of the precipitate gave the title compound (43 g, 56%).

Workup

customThe toluene layer was separated
concentrationconcentrated to 110 ml
additionthen diluted with ethyl acetate (150 ml)
additionA solution of methanesulphonic acid (16.6 g, 0.172M) in ethyl acetate (20 ml) was added
additionMore ethyl acetate (100 ml) was added
filtrationfiltration of the precipitate

Sources & evidence

ORD record: ord-0f30691268ca44be918bb9d9fd101fac
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04661507

Linked notes

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