Water → 3-Azido-7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

HRID 1591437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1591437
I[CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:14].[N-:15]=[N+:16]=[N-:17].CN(C)C(=[NH2+])N(C)C.O>C(Cl)Cl>[N:15]([CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:14])=[N+:16]=[N-:17]

Komponenten

5

Edukt 3

HCID 962WaterHCID 541990513-iodo-7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-oneHCID 178484365HCID 178484365, Verbindung

Produkt 1

HCID 538629013-Azido-7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-oneAusbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

101 mg (0.33 mmol) of 3-iodo-7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (Step B) dissolved in 8.3 mL of methylene chloride and 105 mg (0.66 mmol, 2 eq) of tetramethylguanidinium azide was added. The mixture was stirred at room temperature for 16 hours then water was added and the layers allowed to separate. The organic layer was removed, washed with water and brine, then dried over magnesium sulfate, filtered and solvents removed under vacuum to afford 66 mg (0.30 mmol, 90%) of the product. 1H NMR (200 MHz, CDCl3): 2.28 (m,1H), 2.45 (m,1H), 2.73 (m,1H), 2.93 (m,1H), 3.86 (dd;8,11 Hz;1H), 7.0 (m,3H), 8.15 (br s,1H). FAB-MS: calculated for C10H9FN4O 220; found 221 (M+H,100%).

Aufarbeitung

  1. customto separate
  2. customThe organic layer was removed
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvents removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ad12d909ed054f99986305ed99f2c3ca
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05206235

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