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Triethylamine → 4-Methylamino-3-nitrobenzoic acid-n-phenyl-n-(2-ethoxycarbonylethyl)amide

HRID 50227
Notes
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Reaction equation

HRID 50227 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]([CH2:20][CH2:21][NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:19])[CH3:16].C(N(CC)CC)C>O1CCCC1>[C:23]1([N:22]([CH2:21][CH2:20][C:18]([O:17][CH2:15][CH3:16])=[O:19])[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:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10910393beta-Alanine, N-phenyl-, ethyl esterHCID 179464494-(Methylamino)-3-nitrobenzoyl chloride

Product 1

HCID 109375694-Methylamino-3-nitrobenzoic acid-n-phenyl-n-(2-ethoxycarbonylethyl)amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 24.7 g (0.115 mol) of 4-methylamino-3-nitrobenzoic acid chloride and 22.3 g (0.115 mol) of N-(2-ethoxycarbonylethyl)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 sulfate. 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
  2. distillationthe solvent was 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 sulfate
  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-0c30921ed7b0416bbe609c6ccd10befd
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06710055B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes