m-Tolyl isocyanate → 2-(3-Methylphenylaminocarbonylamino)eth-1-ylamine

HRID 18053

Reaktionsgleichung

Reaktionsgleichung von HRID 18053
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3]C(C)(C)C)=O.[C:12]1([CH3:21])[CH:17]=[CH:16][CH:15]=[C:14]([N:18]=C=O)[CH:13]=1>C(#N)C>[CH3:21][C:12]1[CH:13]=[C:14]([NH:18][C:1]([NH:8][CH2:9][CH2:10][NH2:11])=[O:3])[CH:15]=[CH:16][CH:17]=1

Komponenten

4

Edukt 2

HCID 69303m-Tolyl isocyanateHCID 187201N-BOC-ethylenediamine

Produkt 1

HCID 221388592-(3-Methylphenylaminocarbonylamino)eth-1-ylamineAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

N-Boc-Ethylene diamine (800 mg, 5 mmol) and m-tolyl isocyanate (665 mg, 5 mmol) were dissolved in acetonitrile and the mixture stirred at room temperature for 4 hrs. Solvent was removed under reduced pressure and the residue absorbed onto silica gel; prior to purification by flash column chromatography (silica, hexane:EtOAc 1:1) to yield the desired compound as a white solid (300 mg, 21%) (MS (+ESI, m/e) 294 (M+H)+). The N-Boc protected compound (300 mg, 1.02 mmol) was dissolved in formic acid (10 ml) and the mixture stirred at room temperature overnight. Excess acid was removed to yield the formate salt of the title compound as a white foam (210 mg).

Aufarbeitung

  1. customSolvent was removed under reduced pressure
  2. customthe residue absorbed onto silica gel
  3. customprior to purification by flash column chromatography (silica, hexane:EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-d1500acbc22c4a919f8bedbbebebaaf2
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741328B2

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