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

HRID 9303

反応式

HRID 9303 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-386fea515fe549098d963803cb3d34d0
出典データセット
uspto-grants-2006_08
特許番号
US07091242B2

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