4-Nitrophenol → HCID 18316643, compound

HRID 275808Notes

Reaction equation

HRID 275808 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[CH:10][O:11][C:7]=2[C:6]([C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1.CN(C1C=CC=CN=1)C.[N+:24]([C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1)([O-:26])=[O:25].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[CH:10][O:11][C:7]=2[C:6]([C:12]([O:14][C:30]2[CH:31]=[CH:32][C:27]([N+:24]([O-:26])=[O:25])=[CH:28][CH:29]=2)=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18316645HCID 18316645, compound

Product 1

HCID 18316643HCID 18316643, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-methoxybenzoxazole-7-carboxylic acid (0.16 g), dimethylaminopyridine (catalytic) 4-nitrophenol (0.17 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.17 g) in dichloromethane (30 ml) was stirred at room temperature under nitrogen overnight. The mixture was diluted with dichloromethane (20 ml) and washed with water (2×50 ml). The combined organic phases were dried over magnesium sulphate and evaporated in vacuo to give 4-nitrophenyl 4-methoxybenzoxazole-7-carboxylate. 4-Amino-3,5-dichloropyridine (0.15 g) was dissolved in N,N-dimethylformamide (5 ml) at room temperature under nitrogen. Sodium hydride (40 mg; 60% disopersion in oil) was added, and the mixture stirred for 1 h before addition of the 4-nitrophenyl ester (0.26 g) in N,N-dimethylformamide (20 ml). After stirring for 60 h, the N,N-dimethylformamide was evaporated in vacuo, and the residue partitioned between ethyl acetate (40 ml) and water (40 ml). The combined organic phases were washed with water (2×40 ml), dried over magnesium sulphate, evaporated onto silica and purified by flash chromatography eluting with 50% ethyl acetate in hexane) to yield the title compound as a white solid (51 mg).

Workup

  1. washwashed with water (2×50 ml)
  2. dry with materialThe combined organic phases were dried over magnesium sulphate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-e587942077a340e19947a9344477360a
Source dataset
uspto-grants-2002_03
Patent number
US06353010B1

Reaction notes

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