Water → Carbamic acid, N-(2-bromo-4-methyl-5-thiazolyl)-N-methyl-, 1,1-dimethylethyl ester

HRID 1470413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470413
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[S:12][C:11]([Br:13])=[N:10][C:9]=1[CH3:14])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:19].O>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:15])[N:7]([C:8]1[S:12][C:11]([Br:13])=[N:10][C:9]=1[CH3:14])[CH3:19])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59580681HCID 59580681, Verbindung

Produkt 1

HCID 59580796Carbamic acid, N-(2-bromo-4-methyl-5-thiazolyl)-N-methyl-, 1,1-dimethylethyl esterAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (2-bromo-4-methyl-thiazol-5-yl)-carbamic acid tert-butyl ester (2.93 g, 10 mmol) in DMF (50 mL) at 0° C. was added NaH (480 mg, 12 mmol, 60% dispersion in mineral oil) in one portion and the suspension was stirred for 1 h. Iodomethane (0.65 mL, 10.5 mmol) was added in one portion, and after 5 min the reaction mixture was warmed to ambient temperature and stirred for 5 h. Water and ethyl acetate were added and the resulting biphasic mixture was separated. The aqueous layer was extracted one time with ethyl acetate. The combined organic extracts were washed twice with brine, dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The crude product was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) to give the desired product as a clear oil (1.66 g, 54%): IR (KBr) 1688 cm−1; 1H NMR (300 MHz, CDCl3) δ 2.98 (s, 3H), 2.29 (s, 3H), 1.54 (s, 9H); ESIMS m/z 309 (M+2).

Aufarbeitung

  1. stirringstirred for 5 h
  2. customthe resulting biphasic mixture was separated
  3. extractionThe aqueous layer was extracted one time with ethyl acetate
  4. washThe combined organic extracts were washed twice with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe crude product was purified by silica gel chromatography (0-100% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6444897befdb46188dc628aee78a3610
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006446B2

Notizen zur Reaktion

Wird geladen…