2-Chlorobenzoxazole → Tert-butyl 2-(benzo[d]oxazol-2-ylamino)ethylcarbamate

HRID 447144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 447144
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11]([O:15][C:16](=[O:21])[NH:17][CH2:18][CH2:19][NH2:20])([CH3:14])([CH3:13])[CH3:12]>C(Cl)(Cl)Cl>[O:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:20][CH2:19][CH2:18][NH:17][C:16](=[O:21])[O:15][C:11]([CH3:13])([CH3:12])[CH3:14]

Komponenten

4

Edukt 2

HCID 119862-ChlorobenzoxazoleHCID 187201N-BOC-ethylenediamine

Produkt 1

HCID 47453718Tert-butyl 2-(benzo[d]oxazol-2-ylamino)ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of 2-chlorobenzoxazole (0.6 mL, 5.16 mmol) and N-(2-aminoethyl) carbamic acid tert-butyl ester (2.4328 g, 15.18 mmol)) was stirred in a preheated oil bath at 125° C. for 5 h, then held at room temperature overnight. The solidified mixture was dissolved in chloroform (125 mL), washed with aqueous sodium bicarbonate (2×150 mL), then brine (1×150). The organic layer was dried over sodium sulfate, then filtered and concentrated in vacuo. The resulting residue was purified by flash column chromatography, eluting with 60% ethyl acetate in heptane to yield tert-butyl 2-(benzo[d]oxazol-2-ylamino)ethylcarbamate as a beige powder.

Aufarbeitung

  1. waitheld at room temperature overnight
  2. washwashed with aqueous sodium bicarbonate (2×150 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by flash column chromatography
  7. washeluting with 60% ethyl acetate in heptane

Quellen und Nachweise

ORD-Eintrag
ord-6c940d0472ba490c9940a6b75fb13a00
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481547B2

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