Hydrochloric Acid → 6-Bromo-5',6'-dihydro-4'H-spiro[chromene-2,3'-pyran]-4(3H)-imine

HRID 1965119

Reaktionsgleichung

Reaktionsgleichung von HRID 1965119
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:15](=[CH:16][CH:17]=1)[O:14][C:8]1([CH2:13][CH2:12][CH2:11][O:10][CH2:9]1)[CH2:7][C:6]2=[N:18]S(C(C)(C)C)=O>O1CCOCC1>[Br:2][C:3]1[CH:4]=[C:5]2[C:15](=[CH:16][CH:17]=1)[O:14][C:8]1([CH2:13][CH2:12][CH2:11][O:10][CH2:9]1)[CH2:7][C:6]2=[NH:18]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 67979337N-(6-Bromo-5',6'-dihydro-4'H-spiro[chromene-2,3'-pyran]-4(3H)-ylidene)-2-methylpropane-2-sulfinamide

Produkt 1

HCID 679793356-Bromo-5',6'-dihydro-4'H-spiro[chromene-2,3'-pyran]-4(3H)-imine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

HCl (4 M in 1,4-dioxane) (0.395 mL, 12.99 mmol) was added to a suspension of N-(6-bromo-5′,6′-dihydro-4′H-spiro[chromene-2,3′-pyran]-4(3H)-ylidene)-2-methylpropane-2-sulfinamide (Example 45 Step 1, 520 mg, 1.30 mmol) in anhydrous 1,4-dioxane (6 mL) and the resulting mixture was stirred under a nitrogen atmosphere at r.t. for 2 days. A precipitate was formed. The precipitate was filtered off and washed with Et2O. The solid was then dissolved in DCM and sat. aq. NaHCO3. The mixture was poured into a phase separator, the organic layer was collected and concentrated. The title compound was used directly in the next step without any further purification.

Aufarbeitung

  1. customA precipitate was formed
  2. filtrationThe precipitate was filtered off
  3. washwashed with Et2O
  4. dissolutionThe solid was then dissolved in DCM
  5. additionThe mixture was poured into a phase separator
  6. customthe organic layer was collected
  7. concentrationconcentrated
  8. customThe title compound was used directly in the next step without any further purification

Quellen und Nachweise

ORD-Eintrag
ord-416f759ae202447683cdd9e3514a724a
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415483B2

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