Triethylamine → tert-butyl N-[(2-aminophenyl)methyl]carbamate

HRID 1872904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1872904
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].C(N(CC)CC)C.O1CCOCC1.[C:23](=O)([O:29]C(C)(C)C)[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]>O1CCOCC1.O.C(OCC)(=O)C>[C:25]([O:24][C:23]([NH:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[NH2:1])=[O:29])([CH3:28])([CH3:27])[CH3:26]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 1780962-(Aminomethyl)anilineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Produkt 1

HCID 4409487tert-butyl N-[(2-aminophenyl)methyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

2-Aminobenzylamine (5.0 g, 40.9 mmol) and triethylamine (4.1 g, 40.9 mmol) were dissolved in a mixed solvent (50 ml) of dioxane-water (2:1). A dioxane solution (8.9 g/10 ml) of di-t-butyl carbonate was added dropwise to the solution under cooling with ice water. The mixture was stirred for 2 hours as it was. After the reaction mixture was diluted with ethyl acetate, an aqueous phase was removed, and an organic phase was washed 3 times with water and once with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was crystallized from diisopropyl ether-hexane to obtain 6.70 g of the title compound.

Aufarbeitung

  1. customan aqueous phase was removed
  2. washan organic phase was washed 3 times with water
  3. dry with materialonce with saturated brine, and dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was crystallized from diisopropyl ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-80c123cac2ce4e6d842d744bad8d81a3
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06110967

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