tert-Butanol → tert-Butyl 4-(methylamino)benzoate

HRID 446532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446532
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O-:9])=[O:8])=[CH:5][CH:4]=1.Cl.C(N=C=NCCCN(C)C)C.[C:24](O)([CH3:27])([CH3:26])[CH3:25]>CN(C)C1C=CN=CC=1>[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:8])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 6386tert-ButanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69332534-(Methylamino)benzoate

Produkt 1

HCID 22291264tert-Butyl 4-(methylamino)benzoateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Versuchsvorschrift

4-(Methylamino)benzoate (2.00 g, 13.2 mmol) was dissolved in tert-butanol (66 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (89 mg, 0.464 mmol) and 4-dimethylaminopyridine (81 mg, 0.660 mmol) were added, and the mixture was stirred at room temperature for 17 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1, v/v) to give the title compound (2.14 g; yield, 78%) as a yellow oily substance.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (hexane

Quellen und Nachweise

ORD-Eintrag
ord-34e95d34a9ec49d99e6c07421a7ecd6a
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476253B2

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