4-Nitrobenzoic Acid → 4-Nitrobenzoic acid-n-phenyl-n-(2-methoxycarbonylethyl)amide

HRID 50374Notes

Reaction equation

HRID 50374 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][O:14][C:15]([CH2:17][CH2:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16].C(N(CC)CC)C.C(Cl)Cl.CO>S(Cl)(Cl)=O.CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[C:20]1([N:19]([CH2:18][CH2:17][C:15]([O:14][CH3:13])=[O:16])[C:8](=[O:10])[C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 8471TriethylamineHCID 89103N-Phenyl-beta-alanine methyl esterHCID 21226129Dichloromethane methanol

Product 1

HCID 184123414-Nitrobenzoic acid-n-phenyl-n-(2-methoxycarbonylethyl)amide

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Procedure

16.7 g (0.1 mol) of 4-nitrobenzoic acid were refluxed in 50 mL of thionyl chloride and 3 drops of dimethylformamide for 1 hour. After the solvent had been distilled off in vacuo, the crude product was dissolved in 150 mL of tetrahydrofuran and added dropwise to a solution of 18 g (0.1 mol) of N-(2-methoxycarbonylethyl)aniline in 250 mL of tetrahydrofuran and 42 mL (0.3 mol) of triethylamine. After being stirred for one hour at ambient temperature, the reaction mixture was diluted with 250 mL of ethyl acetate and washed 2× with 200 mL of 14% saline solution. After the solvent had been distilled off and the residue chromatographed (silica gel; methylene chloride), a yellow oil was obtained which slowly solidified. Yield: 32.6 g (100% of theory); Rf value: 0.37 (silica gel; methylene chloride/methanol=50:1).

Workup

  1. distillationAfter the solvent had been distilled off in vacuo
  2. dissolutionthe crude product was dissolved in 150 mL of tetrahydrofuran
  3. washwashed 2× with 200 mL of 14% saline solution
  4. distillationAfter the solvent had been distilled off
  5. customthe residue chromatographed (silica gel; methylene chloride)
  6. customa yellow oil was obtained which

Sources & evidence

ORD record
ord-40ece7a3f3114d3794e09048cb619bd9
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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