Dimethylformamide → HCID 86748269, compound

HRID 2380273Notes

Reaction equation

[CH:1]([O:4][N:5]=[C:6]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)([CH3:3])[CH3:2].Cl[Si:20]([CH3:23])([CH3:22])[CH3:21].[C:24](=O)([O-])[O-].[K+].[K+].CN(C=O)C>[I-].[K+].O>[CH:1]([O:4][N:5]=[C:6]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:21][Si:20]([CH3:23])([CH3:24])[CH3:22])[CH:8]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

2.7 g of 1-(O-isopropyl-3-hydroxybenzohydroximoyl)-1H-1,2,4-triazole, 1.5 g of chlorotrimethylsilane, 1.8 g of potassium carbonate, and a small amount of potassium iodide catalyst were added to 100 ml of DMF. The mixture was stirred for at 90° C. 2 hours. After the resultant mixture was allowed to sit and cool naturally, it was poured into water. The organic layer was extracted with ethyl acetate and dried over magnesium sulfate. The solvent in the organic layer was removed under reduced pressure. The residue was purified by column chromatography (eluate: hexane/ethyl acetate=4/1), thus yielding 3.2 g (yield: 89%) of the desired product (transparent viscous liquid) having a refractive index of [nD20 ] 1.5310 at 20° C.

Workup

custom2 hours
temperaturecool naturally
extractionThe organic layer was extracted with ethyl acetate
dry with materialdried over magnesium sulfate
customThe solvent in the organic layer was removed under reduced pressure
customThe residue was purified by column chromatography (eluate: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-6b8707bba736421bb0c10c148bde33ad
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05366988

Reaction notes

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