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

HRID 358959Notes

Reaction equation

HRID 358959 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-900bb01d1ba843eabfcc282d60563263
Source dataset
uspto-grants-1991_03
Patent number
US04999354

Reaction notes

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