Hydrochloric Acid → 6-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-1(3H)-imine

HRID 1770944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1770944
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH2:13][C:7]1([CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)[C:6]2=[N:17]S(C(C)(C)C)=O.CCOCC>O1CCOCC1>[Br:2][C:3]1[CH:4]=[C:5]2[C:14]([CH2:13][C:7]3([C:6]2=[NH:17])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]3)=[CH:15][CH:16]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67979409N-(5-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-3(1 H)-ylidene)-2-methylpropane-2-sulfinamide

Produkt 1

HCID 679795066-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-1(3H)-imine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

HCl (4M in 1,4-dioxane) (0.683 mL, 2.73 mmol) was added to a solution of N-(5-bromo-2′,3′,5′,6′-tetrahydrospiro[indene-2,4′-pyran]-3(1H)-ylidene)-2-methylpropane-2-sulfinamide (Example 25 Step 1, 105 mg, 0.27 mmol) in anhydrous 1,4-dioxane (1 mL) and the resulting mixture was stirred under a nitrogen atmosphere at r.t. overnight. Et2O (3 mL) was added, the precipitate was filtered off, washed with Et2O and then dissolved in DCM (5 mL) and sat. aq. NaHCO3 (5 mL). The mixture was poured into a phase separator, the organic layer was collected and concentrated to give the title compound that was used in the next step without any further purification.

Aufarbeitung

  1. filtrationthe precipitate was filtered off
  2. washwashed with Et2O
  3. dissolutiondissolved in DCM (5 mL)
  4. additionThe mixture was poured into a phase separator
  5. customthe organic layer was collected
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0b121236d6e648d18795c6ecd321449a
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09248129B2

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