2-Nitroaniline → 2-Nitrophenylurethane

HRID 1197689Notes

Reaction equation

HRID 1197689 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[CH2:11]([O:13][C:14](Cl)=[O:15])[CH3:12]>N1C=CC=CC=1.ClCCl>[CH2:11]([O:13][C:14]([NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2])=[O:15])[CH3:12]

Participants

5

Reactant 2

HCID 69462-NitroanilineHCID 10928Ethyl chloroformate

Product 1

HCID 2479042-NitrophenylurethaneYield 73.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-nitroaniline (6.9 g, 50.0 mmol) in pyridine (6 mL) and dichloromethane (25 mL) at 0° C. under argon was added ethylchloroformate (7.3 mL, 75.0 mmol) through an addition funnel. After the addition was finished, the cooling bath was removed and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate. The combined extracts were washed with water, saturated sodium bicarbonate solution and brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated to yield the title A compound as a yellow solid (7.7 g). 1H NMR (CDCl3) δ 8.55 (d, J=8.0 Hz, 1 H), 8.2 (d, J=8.0 Hz, 1 H), 7.6 (t, J=8.0 Hz, 1 H), 7.1 (t, J=7.5 Hz, 1 H), 4.25 (q, J=6.0 Hz, 2 H), 1.3 (t, J=6.0 Hz, 3 H); 13C NMR (CDCl3) 153.0, 135.8, 135.4, 125.7, 122.1, 120.5, 63.6, 14.3 ppm.

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. additionThe reaction mixture was poured into 2N hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts were washed with water, saturated sodium bicarbonate solution and brine
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f5f38cbaf1f240898345004bdbbda937
Source dataset
uspto-grants-1994_01
Patent number
US05276168

Reaction notes

Loading…