2-Chloroethyl N-(2-chloro-4-nitrophenyl)carbamate → 3-(2-Chloro-4-nitrophenyl)-2-oxazolidinone

HRID 902999Notes

Reaction equation

HRID 902999 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[NH:14][C:15](=[O:20])[O:16][CH2:17][CH2:18]Cl>CO.C(O)C>[Cl:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[N:14]1[CH2:18][CH2:17][O:16][C:15]1=[O:20]

Participants

5

Reactant 2

HCID 3107132-Chloroethyl N-(2-chloro-4-nitrophenyl)carbamateHCID 10942334Sodium Methoxide

Product 1

HCID 233373183-(2-Chloro-4-nitrophenyl)-2-oxazolidinone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 11.25 g of sodium methoxide in 50 ml of methanol was added drop-by-drop to a stirred solution of 58.0 g of 1A in 400 ml of ethanol. The mixture was refluxed for 5 minutes, then the volatile materials were evaporated under reduced pressure. The residue was treated with water and extracted with ether. The extract was dried and concentrated under reduced pressure. The residue was cooled and filtered to give 3-(2-chloro-4-nitrophenyl)-2-oxazolidinone (1B), as a white solid, mp: 94°-96° C.

Workup

  1. temperatureThe mixture was refluxed for 5 minutes
  2. customthe volatile materials were evaporated under reduced pressure
  3. additionThe residue was treated with water
  4. extractionextracted with ether
  5. customThe extract was dried
  6. concentrationconcentrated under reduced pressure
  7. temperatureThe residue was cooled
  8. filtrationfiltered

Sources & evidence

ORD record
ord-0347dc0460dd46d2895dd2d891fb1b40
Source dataset
uspto-grants-1980_10
Patent number
US04226612

Reaction notes

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