Hexachloroethane → HCID 86726479, compound

HRID 1487645Notes

Reaction equation

[CH3:1][C:2]([O:13][Si:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH2:3][N:4]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[N:5]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:28]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:28][C:8]1[N:4]([CH2:3][C:2]([CH3:1])([O:13][Si:14]([CH3:15])([CH3:17])[CH3:16])[CH3:12])[N:5]=[CH:6][C:7]=1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 1-(2-methyl-2-((trimethylsilyl)oxy)propyl)-4-nitro-1H-pyrazole (1 equiv) in THF (0.41 M) was cooled into −78° C., followed by addition of lithium bis(trimethylsilyl)amide (2.6 equiv). After 1 h, hexachloroethane (1.5 equiv) was added. The reaction mixture was stirred at −78° C. for 2 h then the mixture was quenched with saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate and the organic layer was dried over sodium sulfate, filtered and concentrated. The product was purified by silica gel flash chromatography (15% ethyl acetate in petroleum ether) to afford the title compound as a colorless oil (80.1% yield). 1H NMR (400 MHz, CHLOROFORM-d1) δ ppm 8.12 (s, 1H), 4.06 (s, 2H), 1.51 (s, 6H), 0.01 (s, 9H). MS (ESI) m/z 292.1 [M+H]+.

Workup

customthe mixture was quenched with saturated aqueous ammonium chloride solution
extractionThe mixture was extracted with ethyl acetate
dry with materialthe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe product was purified by silica gel flash chromatography (15% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-d54eef42c82d429ea0c44cd40ed88630
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428509B2

Reaction notes

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