Ethylamine → N-ethyl-2-chloro-5-nitrobenzamide

HRID 1167657Notes

Reaction equation

HRID 1167657 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)([N:16]1[CH:20]=[CH:19]N=C1)=O.C(N(CC)CC)C.C(N)C>C1COCC1>[CH2:20]([NH:16][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[Cl:1])[CH3:19]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 8471TriethylamineHCID 172872-Chloro-5-nitrobenzoic acidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 4380195N-ethyl-2-chloro-5-nitrobenzamideYield 45.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-5-nitrobenzoic acid (20 g, 100 mmol) in THF (200 mL) was treated with carbonyldiimidazole (CDI) (17.8 g, 110 mmol) and triethylamine (16 mL, 110 mmol) at room temperature. After 1 hr, a solution of ethylamine (70% in water, 10 mL) was added and the mixture was stirred for 18 h. Solvent was removed by evaporation and the residue was dissolved in methylene chloride, washed with 3% KOH solution followed by water (three times) until the aqueous phase extracts were colorless. The organic phase was dried over MgSO4, filtered, and the filtrate was concentrated to provide 10.4 g of N-ethyl-2-chloro-5-nitrobenzamide as light yellow crystals.

Workup

  1. customSolvent was removed by evaporation
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washwashed with 3% KOH solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-895a572207c54c86ab1669f4b9f811b0
Source dataset
uspto-grants-2003_09
Patent number
US06620827B2

Reaction notes

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