Hydrochloric Acid → Trans-6'-bromo-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-imine

HRID 1965091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1965091
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]1([CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11]1)[C:5]2=[N:18]S(C(C)(C)C)=O.Cl.CCOCC>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8]([CH2:7][C:6]3([CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11]3)[C:5]2=[NH:18])=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67043683N-(5'-bromo-4-methoxyspiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide

Produkt 1

HCID 67979447Trans-6'-bromo-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-imine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a solution of N-(5′-bromo-4-methoxyspiro[cyclohexane-1,2′-indene]-3′(1′H)-ylidene)-2-methylpropane-2-sulfinamide (Example 19 Step 1, mixture of isomers, 2 g, 4.85 mmol) in anhydrous 1,4-dioxane (25 mL) was added 4M HCl in 1,4-dioxane (12.12 mL, 48.50 mmol). A white precipitate was formed immediately and the resulting cloudy mixture was stirred under a nitrogen atmosphere at r.t. for 90 min. Et2O (30 mL) was added and the solid was filtered off and washed with Et2O. The solid was partitioned between DCM (40 mL) and sat. aq. NaHCO3 (40 mL). The phases were separated and the organic layer concentrated. The crude title compound (1.41 g) was used directly in the next step. MS (EI) m/z 307 M+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6381a5454aa448fc9cc96a1eff624cb8
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415483B2

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