Hydrochloric Acid → 7'-Bromo-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-naphthalen]-1'-imine

HRID 1468229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468229
Cl.[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9]3([CH2:21][CH2:20]3)[C:10]2=[N:13]S(C(C)(C)C)=O)=[CH:5][CH:4]=1.C(OCC)C>O1CCOCC1>[Br:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9]3([CH2:21][CH2:20]3)[C:10]2=[NH:13])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86706705N-(7'-Bromo-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-naphthalene]-1'-ylidene)-2-methylpropane-2-sulfinamide2×

Produkt 1

HCID 867067067'-Bromo-3',4'-dihydro-1'H-spiro[cyclopropane-1,2'-naphthalen]-1'-imineAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

HCl (4 M in 1,4-dioxane) (8.38 mL, 33.5 mmol) was added to a warm solution of N-(7′-bromo-3′,4′-dihydro-1′H-spiro[cyclopropane-1,2′-naphthalene]-1′-ylidene)-2-methylpropane-2-sulfinamide (Intermediate 10, 1.19 g, 3.35 mmol) in dry dioxane (12 mL) under Ar (g). The mixture was stirred at r.t. for 40 min after which diethyl ether was added. The precipitate was filtered and washed with diethyl ether and then taken up in CH2Cl2 and washed twice with sat. aq. NaHCO3. The organic phase was dried (Na2SO4), filtered and concentrated to give the title compound (0.717 g, 85% yield). MS (ES+) m/z 250.0 [M+H]+.

Aufarbeitung

  1. additionwas added
  2. filtrationThe precipitate was filtered
  3. washwashed with diethyl ether
  4. washwashed twice with sat. aq. NaHCO3
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-327990ddbc064184b3fa8d09b7a18566
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000184B2

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