Sodium hydride → HCID 59808428, Verbindung

HRID 1010578

Reaktionsgleichung

Reaktionsgleichung von HRID 1010578
[H-].[Na+].[I:3]C1NC=CN=1.Cl[CH2:10][CH2:11][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:14])[CH3:13].C[N:24]1[CH2:29]CC[N:26]([CH3:30])[C:25]1=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[I:3][C:30]1[N:26]=[CH:25][N:24]([CH2:10][CH2:11][C:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:14])[CH3:13])[CH:29]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-2×HCID 27734682-iodo-1H-imidazoleHCID 57429079tert-butyl N-(4-chloro-2-methylbutan-2-yl)carbamate

Produkt 1

HCID 59808428HCID 59808428, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 67553Tetrabutylammonium IodideKatalysator

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

0.556 g (22.0 mmol) sodium hydride were added batchwise to a solution of 3.88 g (20.0 mmol) iodoimidazole in 30 mL 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone at 5° C. with vigorous stirring. After the development of gas had ended the reaction was stirred for 1 h at 0° C. and 4.44 g (20 mmol) tert-butyl (3-chloro-1,1-dimethyl-propyl)-carbamate in 5 mL 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone and 0.739 g (2.00 mmol) tetrabutylammonium iodide were added. The reaction mixture was stirred for 16 h at ambient temperature, stirred for 24 h at 80° C., cooled to ambient temperature and poured into 750 mL ice water/ethyl acetate 2:1. The phases were separated and the aqueous phase was extracted three times with 150 mL ethyl acetate. The combined organic phases were washed five times with 150 mL water, then once with 150 mL saturated, aqueous sodium chloride solution, dried over sodium sulphate and the solvent was eliminated using the rotary evaporator. The residue was purified by flash column chromatography [petroleum ether/ethyl acetate (80:20→0:100)]. 3.19 g (8.40 mmol, 42%) tert-butyl [3-(4-iodo-imidazol-1-yl)-1,1-dimethyl-propyl]-carbamate were obtained as a colourless oil.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 16 h at ambient temperature
  2. stirringstirred for 24 h at 80° C.
  3. temperaturecooled to ambient temperature
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted three times with 150 mL ethyl acetate
  6. washThe combined organic phases were washed five times with 150 mL water
  7. dry with materialonce with 150 mL saturated, aqueous sodium chloride solution, dried over sodium sulphate
  8. customthe rotary evaporator
  9. customThe residue was purified by flash column chromatography [petroleum ether/ethyl acetate (80:20→0:100)]

Quellen und Nachweise

ORD-Eintrag
ord-f17c85d8c81648609559f3b4f4f96cb9
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977334B2

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