Hydrochloric Acid → 2,2,2-Trichloroethyl 1-isopropyl-3-(thiophen-2-yl)-1h-pyrazol-5-ylcarbamate

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Reaktionsgleichung

[CH:1]([N:4]1[C:8](C(O)=O)=[CH:7][C:6]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[N:5]1)([CH3:3])[CH3:2].C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.[CH:41](Cl)([OH:45])[CH:42]([Cl:44])[Cl:43].[ClH:47]>O1CCOCC1>[CH:1]([N:4]1[C:8]([NH:19][C:22](=[O:31])[O:45][CH2:41][C:42]([Cl:44])([Cl:43])[Cl:47])=[CH:7][C:6]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[N:5]1)([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To a solution of 1-isopropyl-3-(thiophen-2-yl)-1H-pyrazole-5-carboxylic acid (0.68 g, 2.9 mmol) in dioxane (10 mL) was added with triethylamine (0.44 g, 4.3 mmol), diphenylphosphorylazide (0.95 g, 3.5 mmol) and trichloroethanol (0.86 g, 5.8 mmol) and the mixture was heated to 90° C. for 4 h. The mixture was poured into 3 M HCl (40 mL) solution and the product was extracted with EtOAc (2×40 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo. Purification by silica gel chromatography provided 2,2,2-trichloroethyl 1-isopropyl-3-(thiophen-2-yl)-1H-pyrazol-5-ylcarbamate (0.88 g, 80% yield) as a white solid. 1H NMR (400 MHz, Acetone-d6): δ 7.36-7.34 (m, 3H), 7.07 (dd, J=5.6 Hz, 4.0 Hz, 1H), 6.52 (s, 1H), 5.83 (t, J=7.2 Hz, 3H), 4.95 (s, 2H), 4.66-4.62 (m, 1H), 1.45 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 382.0 (M+H+).

Aufarbeitung

extractionthe product was extracted with EtOAc (2×40 mL)
washThe combined organics were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-c0c9cca43ad8428dbf78179843149592
Quelldatensatz: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08188113B2

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