Ammonium cerium (IV) nitrate → 5,6,7,8-tetrahydro-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one

HRID 1529567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1529567
[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.COC1C=CC(C[N:32]2[CH2:38][CH2:37][CH2:36][C:35]3[N:39]=[C:40]([CH2:42][O:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[S:41][C:34]=3[C:33]2=[O:50])=CC=1>O.C(#N)C>[O:43]([CH2:42][C:40]1[S:41][C:34]2[C:33](=[O:50])[NH:32][CH2:38][CH2:37][CH2:36][C:35]=2[N:39]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Komponenten

5

Edukt 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 666085925,6,7,8-tetrahydro-5-[(4-methoxyphenyl)methyl]-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one

Produkt 1

HCID 532467235,6,7,8-tetrahydro-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-oneAusbeute 52,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of ammonium cerium (IV) nitrate (1.08 g, 1.97 mmol) in H2O (1.5 mL) was added to a stirred solution of 5,6,7,8-tetrahydro-5-[(4-methoxyphenyl)methyl]-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one (0.22 g, 0.56 mmol) in ACN (5 mL). The mixture was stirred at room temperature for 16 hours and then diluted with H2O and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo to yield 5,6,7,8-tetrahydro-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one (0.081 g, 52%) as a white solid. C14H14N2O2S LCMS: Rt 1.59, m/z 275 [M+H]+ (using method, LC-MS Method 6).

Aufarbeitung

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a69ab4acb9164ad68c63f9e85a9d469f
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090632B2

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