Dicyclohexylcarbodiimide → Benzoic acid, 3-amino-5-nitro-, ethyl ester

HRID 2095101

Reaction equation

HRID 2095101 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[CH2:14]1CCC(N=C=NC2CCCCC2)C[CH2:15]1>CCO>[CH2:14]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=[C:2]([NH2:1])[CH:3]=1)[CH3:15]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 2393423-Amino-5-nitrobenzoic acid

Product 1

HCID 826201Benzoic acid, 3-amino-5-nitro-, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Amino-5-nitrobenzoic acid (910 mg, 5.0 mmol) was dissolved in EtOH (25 mL). DCC (1.51 g, 7.3 mmol) was added, and the mixture was stirred under reflux overnight. The solid precipitation was filtered off and the filtrate was evaporated. The residue was triturated in the solvent mixture ether:hexane:ethyl acetate, 5:5:1. The title compound was isolated as a fine light yellow powder (0.9 g, 85.7%).

Workup

  1. temperatureunder reflux overnight
  2. customThe solid precipitation
  3. filtrationwas filtered off
  4. customthe filtrate was evaporated
  5. customThe residue was triturated in the solvent mixture ether

Sources & evidence

ORD record
ord-f515d0739ec546ff8cbd60c893927959
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Linked notes

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