Triethylamine → N-ethoxalyl-N-isopropyl-2-nitroaniline

HRID 1073080Notes

Reaction equation

HRID 1073080 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:21](Cl)([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:22]>O1CCCC1>[C:21]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 10583518N-Isopropyl-2-nitroaniline

Product 1

HCID 14853709N-ethoxalyl-N-isopropyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred ice-cooled solution of 2-isopropylamino-nitrobenzene (19.5 g, 0.1 mole) and triethylamine (15 ml 0.11 mole) in tetrahydrofurane (THF, 200 ml) was dropwise added ethoxalyl chloride. The ice bath was removed and the mixture was heated to reflux for 3 hours. The precipitated triethylammonium chloride was filtered off and the filtrate was evaporated in vacuo to give the title compound as an oil.

Workup

  1. customThe ice bath was removed
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 3 hours
  4. filtrationThe precipitated triethylammonium chloride was filtered off
  5. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-dcd550a6b27c4a669a01a4a7880fe1e5
Source dataset
uspto-grants-1990_11
Patent number
US04968682

Reaction notes

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