Diisopropylamine → HCID 15868667, compound

HRID 565170Notes

Reaction equation

HRID 565170 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([O:12][C:13](Cl)=[O:14])[CH3:11])([O-:3])=[O:2].[CH:16]([NH:19][CH:20]([CH3:22])[CH3:21])([CH3:18])[CH3:17]>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([O:12][C:13]([N:19]([CH:20]([CH3:22])[CH3:21])[CH:16]([CH3:18])[CH3:17])=[O:14])[CH3:11])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 7912DiisopropylamineHCID 15403278HCID 15403278, compound

Product 1

HCID 15868667HCID 15868667, compoundYield 57%

Procedure

1-(2-Nitrophenyl)-1-ethoxycarbonyl chloride (XIV; R3=H, R4=CH3; 1.4 g; 6 mmol) was dissolved in diisopropylamine (30 ml) under an inert atmosphere and the solution was refluxed for 48 hr. The resulting diisopropylammonium chloride was filtered off and excess of diisopropylamine was removed by evaporation under vacuum to give an oil, which was purified by flash chromatography on silica, eluting with dichloromethane to afford the required compound as a colourless solid. Recrystallization from toluene-petroleum ether (bp 60-80° C.) 2:1 gave colourless crystals (1.0 g; 57% yield), mp 40-41° C.

Workup

  1. temperaturethe solution was refluxed for 48 hr
  2. filtrationThe resulting diisopropylammonium chloride was filtered off and excess of diisopropylamine
  3. customwas removed by evaporation under vacuum
  4. customto give an oil, which
  5. customwas purified by flash chromatography on silica
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-5e761aa1caf84bf7a28ee37601ba4ad0
Source dataset
uspto-grants-2001_01
Patent number
US06171756B2

Reaction notes

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