Potassium Carbonate → Tert-butyl 4-((2,2-diethoxyethylamino)methyl)benzo[d]thiazol-2-ylcarbamate

HRID 2361958Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2361958
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][NH2:6])[CH3:2].Br[CH2:11][C:12]1[C:17]2[N:18]=[C:19]([N:21](C(OC(C)(C)C)=O)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[S:20][C:16]=2[CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][NH:6][CH2:11][C:12]1[C:17]2[N:18]=[C:19]([NH:21][C:22](=[O:23])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[S:20][C:16]=2[CH:15]=[CH:14][CH:13]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 695242,2-DiethoxyethylamineHCID 670752054-Bromomethyl-2-bis(tert-butoxycarbonyl)aminobenzothiazole

Produkt 1

HCID 86658802Tert-butyl 4-((2,2-diethoxyethylamino)methyl)benzo[d]thiazol-2-ylcarbamateAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2,2-diethoxyethanamine (8.72 ml, 60.0 mmol) in acetonitrile (300 ml) were added 4-bromomethyl-2-bis(tert-butoxycarbonyl)aminobenzothiazole (Compound XIX-1) (1.33 g, 3.00 mmol) and potassium carbonate (3.14 g, 18.0 mmol) and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate (300 ml) and the mixture was washed with water (300 ml) and brine (200 ml). The organic layer was dried over magnesium sulfate (5 g) and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (eluent: chloroform:methanol=100:0 to 80:20) to obtain the title compound (1.01 g, yield: 85%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with ethyl acetate (300 ml)
  3. washthe mixture was washed with water (300 ml) and brine (200 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate (5 g)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography (eluent: chloroform:methanol=100:0 to 80:20)

Quellen und Nachweise

ORD-Eintrag
ord-32e9348fe64b4f57b255c7f5c05b65dd
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691819B2

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