Sodium Sulfate → 2-Hydroxyimino-N-{4-[2-(2-oxo-oxazolidin-3-yl)ethyl]phenyl}acetamide

HRID 44296Notes

Reaction equation

HRID 44296 reaction equation
S([O-])([O-])(=O)=O.[Na+].[Na+].[OH2:8].Cl[C:10](Cl)(Cl)[CH:11]=[O:12].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][N:24]2[CH2:28][CH2:27][O:26][C:25]2=[O:29])=[CH:18][CH:17]=1.Cl.[NH2:31]O>O.Cl>[OH:8][N:31]=[CH:10][C:11]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][N:24]2[CH2:28][CH2:27][O:26][C:25]2=[O:29])=[CH:18][CH:17]=1)=[O:12]

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochlorideHCID 107034763-(2-(4-Aminophenyl)ethyl)-1,3-oxazolidin-2-oneHCID 205283762,2,2-Trichloroacetaldehyde hydrate

Product 1

HCID 866624332-Hydroxyimino-N-{4-[2-(2-oxo-oxazolidin-3-yl)ethyl]phenyl}acetamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

Sodium sulphate (78.3 g) is added to a solution of trichloroacetaldehyde hydrate (32.5 mmoles) in water (100 ml). To the resulting suspension there are added a solution of 3-[2-(4-amino-phenyl)ethyl]oxazolidin-2-one in water (20 ml) and concentrated HCl solution (2.83 ml). A solution of hydroxylamine hydrochloride (95 mmoles) in water (50 ml) is then added. The reaction mixture is heated at reflux for two hours. The mixture is then cooled to ambient temperature. The solid formed is then filtered off, washed with water and dried in vacuo in the presence of P2O5 and at 40° C. overnight to yield the title product, which is used directly in the next Step.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for two hours
  3. customThe solid formed
  4. filtrationis then filtered off
  5. washwashed with water
  6. dry with materialdried in vacuo in the presence of P2O5 and at 40° C. overnight

Sources & evidence

ORD record
ord-487f88ec2cbf40ff8accf80c7ce6dbb9
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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