2-Tolyl isocyanate → Tert-butyl 4-({[(2-methylphenyl)amino]carbonyl}amino)benzylcarbamate

HRID 1829995

Reaktionsgleichung

Reaktionsgleichung von HRID 1829995
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[O:10].[C:11]([O:15][C:16](=[O:26])[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)([CH3:14])([CH3:13])[CH3:12]>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][NH:17][C:16](=[O:26])[O:15][C:11]([CH3:13])([CH3:14])[CH3:12])=[CH:20][CH:21]=1)=[O:10]

Komponenten

4

Edukt 2

HCID 691942-Tolyl isocyanateHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamate

Produkt 1

HCID 21032485Tert-butyl 4-({[(2-methylphenyl)amino]carbonyl}amino)benzylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Methylphenylisocyanate (7.57 g, 59.83 mmol) was added dropwise at 0° C. to a solution of (4-amino-benzyl)-carbamic acid tert-butyl ester (13.30 g, 59.83 mmol, prepared analoguous to: Moloney, Gerard P.; Martin, Graeme R.; Mathews, Neil; Mine, Aynsley; Hobbs, Heather; et al. J. Med Chem. 1999, 42, 2504–2526) in 120 mL DCM. The reaction was heated under reflux for 16 h, cooled to r.t. and the precipitated product was collected by filtration and dried in vacuum (19.20 g, 54.00 mmol). M.p. 200–202° C.; TLC (PE/EtOAc 1/1) Rf 0.65; 1H NMR (400 MHz, D6-DMSO) δ 1.39 (s, 9H); 2.24 (s, 3H); 4.06 (d, J=6 Hz, 2H); 6.93 (mc, 1H); 7.12–7.17 (m, 4); 7.32 (mc, 1H); 7.40 (mc, 2H); 7.85 (mc, 1H); 7.90 (s, 1H); 8.98 (s, 1H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 16 h
  3. filtrationthe precipitated product was collected by filtration
  4. customdried in vacuum (19.20 g, 54.00 mmol)

Quellen und Nachweise

ORD-Eintrag
ord-280c85da84f0492bae20d2d6acbe1fec
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064229B2

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