3,5-Dinitrobenzoyl chloride → N-(3,5-dinitrobenzoyl)-N-(2-ethoxy-2-oxoethyl)glycine ethyl ester

HRID 488282Notes

Reaction equation

HRID 488282 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[NH:16]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(N(CC)CC)C>C(Cl)Cl>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][N:16]([C:7](=[O:8])[C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=1)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:22]

Participants

5

Reactant 3

HCID 74323,5-Dinitrobenzoyl chlorideHCID 8471TriethylamineHCID 80502Diethyl iminodiacetate

Product 1

HCID 19091872N-(3,5-dinitrobenzoyl)-N-(2-ethoxy-2-oxoethyl)glycine ethyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5.0 g (21.7 mmol) of 3,5-dinitrobenzoyl chloride in 75 ml of methylene chloride was added dropwise with stirring to an ice bath cooled mixture of 4.7 ml (27 mmol) of diethyl iminodiacetate and 6.0 ml (43 mmol) of triethylamine in 25 ml of methylene chloride. The reaction mixture was stirred in the cooling bath for 30 minutes and then was left at room temperature for 21 hours. After washing with NaHCO3 solution, the organic layer was dried and concentrated to an oil which was chromatographed on 150 g of silica gel using 20-30% ethyl acetate-hexane. The combined pure fractions were recrystallized from methanol to give 5.95 g (72% yield, 79°-80°) of N-(3,5-dinitrobenzoyl)-N-(2-ethoxy-2-oxoethyl)glycine ethyl ester. The nmr and mass spectra were consistent with the structure.

Workup

  1. temperaturecooled
  2. stirringThe reaction mixture was stirred in the cooling bath for 30 minutes
  3. washAfter washing with NaHCO3 solution
  4. customthe organic layer was dried
  5. concentrationconcentrated to an oil which
  6. customwas chromatographed on 150 g of silica gel using 20-30% ethyl acetate-hexane
  7. customThe combined pure fractions were recrystallized from methanol

Sources & evidence

ORD record
ord-ee175b2a46414dd5aaaf0d90285dc795
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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