Cesium carbonate → N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine

HRID 1258553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258553
[OH:1][N:2]=[C:3]([N:10]1[C:14]([CH3:15])=[N:13][N:12]=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:22][C:23]1[S:24][CH:25]=[C:26]([CH2:28]Br)[N:27]=1>CC#N>[Br:22][C:23]1[S:24][CH:25]=[C:26]([CH2:28][O:1][N:2]=[C:3]([N:10]2[C:14]([CH3:15])=[N:13][N:12]=[N:11]2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:27]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 5003633N-hydroxy-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimineHCID 533022182-Bromo-4-(bromomethyl)-1,3-thiazole

Produkt 1

HCID 86653111N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimineAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of N-hydroxy-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine (2.0 g, 9.84 mmol, 1.0 eq.) in 50 ml of MeCN was added Cs2CO3 (3.52 g, 10.82 mmol, 1.2 eq.) followed by KI (0.163 g, 0.984 mmol, 0.1 eq.) in one portion. The resulting suspension was stirred for 5 mins before addition of 2-bromo-4-(bromomethyl)-1,3-thiazole (2.52 g, 9.84 mmol, 1 eq.) in one portion. The reaction was stirred for 24 hrs at room temperature. The solvent was evaporated then the residue was dissolved in EtOAc and washed with H2O. The organic layer was separated, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine (3.3 g, 88% yield) as a yellow viscous oil.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4bcb1ee92eee4493a3df100fcda67341
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466176B2

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