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

HRID 1829995

Reaction equation

HRID 1829995 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-280c85da84f0492bae20d2d6acbe1fec
Source dataset
uspto-grants-2006_06
Patent number
US07064229B2

Linked notes

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