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

HRID 9303

Reaction equation

HRID 9303 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; Milne, 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-386fea515fe549098d963803cb3d34d0
Source dataset
uspto-grants-2006_08
Patent number
US07091242B2

Linked notes

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