Triethylamine → N-tert-butyl-N-ethoxalyl-2-nitroaniline

HRID 358952Notes

Reaction equation

HRID 358952 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[NH:6][C:7]([CH3:10])([CH3:9])[CH3:8])([O-:3])=[O:2].C(N(CC)CC)C.[C:22](Cl)([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:23]>O1CCCC1>[C:7]([N:6]([C:22]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:23])[C:5]1[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=1[N+:1]([O-:3])=[O:2])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 10797892N-tert-Butyl-2-nitroaniline

Product 1

HCID 20065638N-tert-butyl-N-ethoxalyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-nitro-N-tert-butylaniline (37 g) and triethylamine (35 ml) in tetrahydrofuran (400 ml) was added dropwise a solution of ethoxalyl chloride (25 ml) in tetrahydrofuran (50 ml). The mixture was then brought to reflux temperature for 8 h. The solvent was removed by evaporation, and the residue was partitioned between ether (300 ml) and water (500 ml). The organic phase was washed twice with water, dried over Na2SO4 and evaporated. This left the title compound as light yellow crystals, m.p. 73°-74° C.

Workup

  1. temperatureto reflux temperature for 8 h
  2. customThe solvent was removed by evaporation
  3. customthe residue was partitioned between ether (300 ml) and water (500 ml)
  4. washThe organic phase was washed twice with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. waitThis left the title compound as light yellow crystals, m.p. 73°-74° C.

Sources & evidence

ORD record
ord-231e8e5054254f97a84ddcc59e54f853
Source dataset
uspto-grants-1991_03
Patent number
US04999353

Reaction notes

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