4-Nitrophenol → HCID 18316632, compound

HRID 275807Notes

Reaction equation

HRID 275807 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[C:11]([C:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([O:15][CH3:16])[C:6]=2[N:7]=1)[CH3:2].[N+:17]([C:20]1[CH:25]=[CH:24][C:23](O)=[CH:22][CH:21]=1)([O-:19])=[O:18].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([C:3]1[O:4][C:5]2[C:11]([C:12]([O:14][C:23]3[CH:24]=[CH:25][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=3)=[O:13])=[CH:10][CH:9]=[C:8]([O:15][CH3:16])[C:6]=2[N:7]=1)[CH3:2]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18316646HCID 18316646, compound

Product 1

HCID 18316632HCID 18316632, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Ethyl-4-methoxybenzoxazole-7-carboxylate (1.24 g), 4-dimethylaminopyridine (catalytic), 4-nitrophenol (1.17 g), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.6 g) in dichloromethane (60 ml) were stirred at room temperature for 48 h. The mixture was evaporated onto silica and chromatographed, eluting with 50% ethyl acetate in hexane, to yield 4-nitrophenyl 2-ethyl-4-methoxybenzoxazole-7-carboxylate. 4-Amino-3,5-dichloropyridine (0.57 g) was dissolved in N,N-dimethylformamide (20 ml) at room temperature under nitrogen. Sodium hydride (0.20 g, 60% dispersion) was added, and the mixture stirred for 5 h before addition of the 4-nitrophenyl ester (1.2 g) and stirred for a further 18 h. The reaction mixture was evaporated onto silica and and purified by flash chromatography eluting with 50% ethyl acetate in hexane to separate the title compound as a white solid (0.44 g).

Workup

  1. customThe mixture was evaporated onto silica
  2. customchromatographed
  3. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f9b6a83c5ab44a70885ecbd172aaa1b2
Source dataset
uspto-grants-2002_03
Patent number
US06353010B1

Reaction notes

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