Triethylamine → 4-Methylamino-3-nitro-benzoic acid-n-phenyl-n-(2-ethoxy-carbonylethyl)-amide

HRID 2288357Notes

Reaction equation

HRID 2288357 reaction equation
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[CH2:15]([O:17][C:18](=[C:27]=[O:28])[CH2:19][NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:16].C(N(CC)CC)C>O1CCCC1>[C:21]1([N:20]([CH2:19][C:18](=[C:27]=[O:28])[O:17][CH2:15][CH3:16])[C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([NH:2][CH3:1])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 179464494-(Methylamino)-3-nitrobenzoyl chlorideHCID 86755521N-(2-ethoxy-carbonylethyl)aniline

Product 1

HCID 881838074-Methylamino-3-nitro-benzoic acid-n-phenyl-n-(2-ethoxy-carbonylethyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 24.7 g (0.115 mol) of 4-methylamino-3-nitro-benzoic acid chloride and 22.3 g (0.115 mol) of N-(2-ethoxy-carbonylethyl)-aniline in 300 ml of tetrahydrofuran, 13.1 g (0.13 mol) of triethylamine were added dropwise in 15 minutes, with stirring, at room temperature. After 2 hours stirring the solvent was distilled off in a water-jet vacuum and the residue was mixed with 700 ml of water with stirring. The mixture was extracted 3 times with 200 ml of dichloromethane, the organic extract was washed twice with 200 ml of 2N hydrochloric acid and twice with 300 ml of water and dried over sodium sulphate. The solvent was then distilled off and the oily product thus obtained was purified by column chromatography (1 kg silica gel; eluant: petroleum ether/ethyl acetate=2:1). Yield: 35.0 g (82% of theory), Rf value: 0.28 (silica gel; dichloromethane/ethanol=50:1)

Workup

  1. stirringAfter 2 hours stirring the solvent
  2. distillationwas distilled off in a water-jet vacuum
  3. additionthe residue was mixed with 700 ml of water
  4. stirringwith stirring
  5. extractionThe mixture was extracted 3 times with 200 ml of dichloromethane
  6. extractionthe organic extract
  7. washwas washed twice with 200 ml of 2N hydrochloric acid and twice with 300 ml of water
  8. dry with materialdried over sodium sulphate
  9. distillationThe solvent was then distilled off
  10. customthe oily product thus obtained
  11. customwas purified by column chromatography (1 kg silica gel; eluant: petroleum ether/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-1d41ed5a7eb44b95874c96566f77b567
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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