Dichloromethane → 3-[(4-Aminophenyl)methyl]-1,3-oxazolidin-2-one

HRID 44272Notes

Reaction equation

HRID 44272 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:13][CH2:12][O:11][C:10]2=[O:14])=[CH:6][CH:5]=1)([O-])=O.O.O.Cl[Sn]Cl.[OH-].[Na+].C(Cl)Cl>C(O)C>[NH2:1][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:13][CH2:12][O:11][C:10]2=[O:14])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 666364983-(4-Nitro-benzyl)-oxazolidin-2-one

Product 1

HCID 186245603-[(4-Aminophenyl)methyl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the compound obtained in Step A (0.244 mol) and SnCl2.2H2O (1.0 mol) in ethanol (300 ml) is stirred at reflux for 20 minutes. The solution is brought to 0° C. and made alkaline at pH=10-12 with aqueous sodium hydroxide solution; 500 ml of DCM are added and the emulsion obtained is filtered over Celite. The filtrate is then extracted with DCM (2×300 ml); the organic phases are combined. The organic phase obtained is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate and then filtered. The filtrate obtained is evaporated to dryness to yield the title product, which is used directly in the next Step.

Workup

  1. temperatureat reflux for 20 minutes
  2. customis brought to 0° C.
  3. customthe emulsion obtained
  4. filtrationis filtered over Celite
  5. extractionThe filtrate is then extracted with DCM (2×300 ml)
  6. customThe organic phase obtained
  7. washis washed with water and with saturated aqueous NaCl solution
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. customThe filtrate obtained
  11. customis evaporated to dryness

Sources & evidence

ORD record
ord-d6f4a02d83184fd6991d4bb18eb6c3d5
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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