Hydrochloric Acid → 6'-Bromospiro[cyclobutane-1,2'-inden]-1'(3'H)-imine

HRID 539372

Reaktionsgleichung

Reaktionsgleichung von HRID 539372
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7]1([CH2:14][CH2:13][CH2:12]1)[C:6]2=[N:15]S(C(C)(C)C)=O.CCOCC>O1CCOCC1>[Br:2][C:3]1[CH:4]=[C:5]2[C:9]([CH2:8][C:7]3([CH2:14][CH2:13][CH2:12]3)[C:6]2=[NH:15])=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67979440N-(5'-Bromospiro[cyclobutane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide

Produkt 1

HCID 679793936'-Bromospiro[cyclobutane-1,2'-inden]-1'(3'H)-imine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Hydrochloric acid (4M in 1,4-dioxane, 14.89 mL, 59.55 mmol) was added to a solution of N-(5′-bromospiro[cyclobutane-1,2′-indene]-3′(1′H)-ylidene)-2-methylpropane-2-sulfinamide (Example 54 Step 1, 2.11 g, 5.96 mmol) in anhydrous 1,4-dioxane (60 mL), and the resulting mixture was stirred under an argon atmosphere for 3 h. Et2O (4 mL) was added and the precipitate was filtered off and washed with Et2O, then partitioned between DCM (100 mL), and sat. aq. NaHCO3 (100 mL). The phases were separated and the organic layer concentrated to afford the title compound that was used as such without further purification.

Aufarbeitung

  1. filtrationthe precipitate was filtered off
  2. washwashed with Et2O
  3. custompartitioned between DCM (100 mL), and sat. aq. NaHCO3 (100 mL)
  4. customThe phases were separated
  5. concentrationthe organic layer concentrated

Quellen und Nachweise

ORD-Eintrag
ord-788d506ef8c542168618e4e53b73b0e8
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865911B2

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