Ammonium Chloride → 4-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol

HRID 1622676

Reaktionsgleichung

Reaktionsgleichung von HRID 1622676
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[C:38]3=[N:39][S:40](=[O:44])(=[O:43])[CH2:41][CH2:42][N:37]3[CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=1)(C(C)(C)C)(C)C.[NH4+].[Cl-]>C1COCC1>[O:44]=[S:40]1(=[O:43])[CH2:41][CH2:42][N:37]2[CH:36]=[CH:35][CH:34]=[C:33]([C:30]3[CH:31]=[CH:32][C:27]([OH:26])=[CH:28][CH:29]=3)[C:38]2=[N:39]1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 667477259-(4-((Tert-butyl(dimethyl)silyl)oxy)phenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

Produkt 1

HCID 667478174-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenolAusbeute 96,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

TBAF (1 M in THF) (40.0 mL) was added to a solution of 9-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (14.9 g) in THF (dry)(2.0 L) at 0° C. and the mixture was stirred at ambient temperature for 30 min. The mixture was neutralized with sat. NH4Cl aq. and extracted with EtOAc. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was washed with EtOAc/hexane to give the title compound (10.2 g) as an off-white crystal.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. washThe residue was washed with EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-d8080b96cc5145bfb0d656910390739b
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778934B2

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