Hydrochloric Acid → 5-Bromo-4'-methoxy-3H-spiro[benzofuran-2,1'-cyclohexan]-3-imine

HRID 1770958

Reaktionsgleichung

Reaktionsgleichung von HRID 1770958
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:16][C:8]3([CH2:13][CH2:12][CH:11]([O:14][CH3:15])[CH2:10][CH2:9]3)[C:7](=[N:17]S(C(C)(C)C)=O)[C:6]=2[CH:24]=1.Cl.CCOCC>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:16][C:8]3([CH2:9][CH2:10][CH:11]([O:14][CH3:15])[CH2:12][CH2:13]3)[C:7](=[NH:17])[C:6]=2[CH:24]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67979520N-(5-Bromo-4'-methoxy-3H-spiro[benzofuran-2,1'-cyclohexane]-3-ylidene)-2-methylpropane-2-sulfinamide

Produkt 1

HCID 679795445-Bromo-4'-methoxy-3H-spiro[benzofuran-2,1'-cyclohexan]-3-imineAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a solution of N-(5-bromo-4′-methoxy-3H-spiro[benzofuran-2,1′-cyclohexane]-3-ylidene)-2-methylpropane-2-sulfinamide (Example 29 Step 1, 2 g, 4.83 mmol) in anhydrous 1,4-dioxane (40 mL) was added 4M HCl in 1,4-dioxane (12.07 mL, 48.27 mmol) and the resulting mixture was stirred under a nitrogen atmosphere at rt overnight. Et2O (30 mL) was added and the precipitate was filtered off and washed with Et2O, then partitioned between DCM (40 mL) and sat. aq. NaHCO3 (40 mL). The phases were separated and the organic layer concentrated, yielding 1.37 g of the crude title compound which was used immediately in the next step: MS (EI) m/z 309 M+.

Aufarbeitung

  1. filtrationthe precipitate was filtered off
  2. washwashed with Et2O
  3. custompartitioned between DCM (40 mL) and sat. aq. NaHCO3 (40 mL)
  4. customThe phases were separated
  5. concentrationthe organic layer concentrated

Quellen und Nachweise

ORD-Eintrag
ord-3febc73c012241a58e39d24b34a7cb37
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09248129B2

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