Nitrogen → 2-Bromo-5-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

HRID 1044753

Reaktionsgleichung

Reaktionsgleichung von HRID 1044753
N#N.[Br:3][C:4]1[S:5][C:6]([C:9](=[O:11])[CH3:10])=[CH:7][N:8]=1.COC([O:17][CH3:18])OC.[C:19]([O-])(O)=O.[Na+]>C(O)CO>[Br:3][C:4]1[S:5][C:6]([C:9]2([CH3:10])[O:17][CH2:18][CH2:19][O:11]2)=[CH:7][N:8]=1

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 575628131-(2-Bromo-1,3-thiazol-5-yl)ethan-1-one

Produkt 1

HCID 668200782-Bromo-5-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and a condenser under inert atmosphere (N2), a solution of 1-(2-bromo-thiazol-5-yl)-ethanone (16.22 g, 78.71 mmol) in ethylene glycol (85 mL) was treated with trimethylorthoformate (18 mL, 164.19 mmol) followed by LiBF4 (1.51 g, 15.74 mmol). The reaction mixture was heated at 95° C. for 2 days. Sat. aq. NaHCO3 was added and the mixture was extracted with Et2O (3×). The org. extracts were washed with brine, dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 to 3:1 hept-EA) gave the title compound as a yellow solid. TLC:rf (1:1 hept-EA)=0.63. LC-MS-conditions 02: tR=0.89 min; [M+H]+=250.24.

Aufarbeitung

  1. extractionthe mixture was extracted with Et2O (3×)
  2. washextracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (20:1 to 3:1 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-310be4375919419b9130be1b8e51e298
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563714B2

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