alpha-Naphthyl isocyanate → HCID 15698065, compound

HRID 653900Notes

Reaction equation

HRID 653900 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([O:23][CH3:24])=[O:22])=[CH:11][CH:10]=2)[C:6]([CH2:25][CH2:26][CH2:27][CH3:28])=[N:5][C:4]=1[Cl:29].[C:30]1([N:40]=[C:41]=[O:42])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1>C(Cl)(Cl)Cl>[CH2:25]([C:6]1[N:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([O:23][CH3:24])=[O:22])=[CH:13][CH:14]=2)[C:3]([CH2:2][NH:1][C:41]([NH:40][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32][CH:31]=2)=[O:42])=[C:4]([Cl:29])[N:5]=1)[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 66589alpha-Naphthyl isocyanateHCID 14697223HCID 14697223, compound

Product 1

HCID 15698065HCID 15698065, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-Aminomethyl-2-butyl-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]-4-chloroimidazole (1.00 g, 2.4 mmol, 1 eq) and 1-naphthyl isocyanate (0.35 mL, 2.4 mmol, 1 eq), were mixed and stirred in chloroform at room temperature for 3 days. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica gel in 1:1 hexane/ethyl acetate to yield 770 mg of a white glass. NMR (200 MHz, CDCl3) δ 7.83 (d, 3H, J=6Hz); 7.67 (d, 1H, J=6Hz); 7.56-7.18 (m, 9H); 6.97 (d, 2H, J=7Hz); 6.74 (s, 1H); 5.27 (s, 2H); 4.74 (s, 1H); 4.39 (d, 2H, J=7Hz); 3.58 (s, 3H); 2.60 (t, 2H, J=7Hz); 1.43-1.21 (m, 4H); 0.85 (t, 3H, J=7Hz).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography over silica gel in 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-87d8d82fe48e4817a3f098b2c803851e
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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