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

HRID 358952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358952
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-231e8e5054254f97a84ddcc59e54f853
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04999353

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