4-Nitroaniline → p-Nitrophenylurethane

HRID 724834

Reaction equation

HRID 724834 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(CC)CC.Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(Cl)(Cl)Cl>[CH2:22]([O:21][C:19]([NH:8][C:7]1[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 74754-NitroanilineHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 230135p-Nitrophenylurethane

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a cooled (0° C.) suspension of 4-nitroaniline (10 g, 0.072 mol) and Et3N (10 mL) in CHCl3 (120 mL), was added dropwise ethyl chloroformate (6.9 mL) and the mixture was stirred under an argon atmosphere at room temperature overnight. CHCl3 was added and the resulting solution was washed with 1N HCl. The layers were separated, the aqueous phase was washed with CHCl3 and the combined organic extracts were dried and concentrated. The residue was chromatographed on silica gel (hexane:EtOAc, 30%) to afford N-(ethoxycarbonyl)-4-nitroaniline (1.7 g).

Workup

  1. temperatureTo a cooled
  2. washthe resulting solution was washed with 1N HCl
  3. customThe layers were separated
  4. washthe aqueous phase was washed with CHCl3
  5. customthe combined organic extracts were dried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (hexane:EtOAc, 30%)

Sources & evidence

ORD record
ord-0aa353dec71e421e93b481f6562f52de
Source dataset
uspto-grants-1998_01
Patent number
US05705504

Linked notes

Loading…