4-Nitrophenol → ethyl N-[2-(4-nitrophenoxy)ethyl]carbamate

HRID 2248195Notes

Reaction equation

HRID 2248195 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].Cl[CH2:14][CH2:15][NH:16][C:17](=[O:21])[O:18][CH2:19][CH3:20].CCOCC>CCCCCC.CN(C=O)C>[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:14][CH2:15][NH:16][C:17](=[O:21])[O:18][CH2:19][CH3:20])=[CH:8][CH:7]=1)([O-:5])=[O:4]

Participants

7

Reactant 4

HCID 9804-NitrophenolHCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 80621Ethyl 2-chloroethylcarbamate

Product 1

HCID 15662591ethyl N-[2-(4-nitrophenoxy)ethyl]carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

To sodium hydride (1.35 g, 56.2 mmol), prewashed in hexane, in 30 ml of DMF is added 4-nitrophenol in 5 ml of DMF at 15°. After anion formation is complete, ethyl N-chloroethylcarbamate (7.12 g, 47.0 mmol) is slowly added. The slurry is heated to 85° and stirred for 17 hours, after which the reaction is cooled to RT, poured into ice water and ether, and extracted with ether. The combined organic layers are washed with 10% sodium hydroxide, with water and with brine, dried and filtered and the solvent is removed by rotoevaporation to give ethyl N-[2-(4-nitrophenoxy)-ethyl]carbamate.

Workup

  1. temperatureThe slurry is heated to 85°
  2. extractionextracted with ether
  3. washThe combined organic layers are washed with 10% sodium hydroxide, with water and with brine
  4. customdried
  5. filtrationfiltered
  6. customthe solvent is removed by rotoevaporation

Sources & evidence

ORD record
ord-6854a6fc995a4918b4a9e9fa1d4869af
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

Loading…