Sodium hydride → 4-Bromo-2-ethoxyphenethyl 3-cyanophenylcarbamate

HRID 735666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735666
[H-].[Na+].[N:3]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10])=[C:4]=[O:5].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[C:17]([O:24][CH2:25][CH3:26])[CH:16]=1>C1COCC1>[C:9]([C:8]1[CH:7]=[C:6]([NH:3][C:4](=[O:5])[O:23][CH2:22][CH2:21][C:18]2[CH:19]=[CH:20][C:15]([Br:14])=[CH:16][C:17]=2[O:24][CH2:25][CH3:26])[CH:13]=[CH:12][CH:11]=1)#[N:10]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 27333153-IsocyanatobenzonitrileHCID 578428372-(4-Bromo-2-ethoxyphenyl)ethan-1-ol

Produkt 1

HCID 688177644-Bromo-2-ethoxyphenethyl 3-cyanophenylcarbamateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

NaH (346 mg, 8.7 mmol, 60% dispersion in oil) was added in one portion to a solution of 3-isocyanatobenzonitrile (567 mmol, 3.9 mmol) and 62E (960 mg, 3.9 mmol) in THF (40 mL) and the cooling bath was removed. After stirring for 2 h at ambient temperature 1.0 N citric acid (50 mL) was added and the mixture was extracted with diethyl ether. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by flash chromatography (0% to 60% EtOAc in hexanes) to yield 62F (611 mg, 50%) as a pale, yellow solid. MS (ESI) m/z 411.0/413.0 (M+H)+.

Aufarbeitung

  1. customthe cooling bath was removed
  2. additionwas added
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography (0% to 60% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2f00d4618ce74415af3ba3ed1d9f4a62
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592331B2

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