Water → 2-(4-Chlorophenoxymethyl)-5-methyl-4-oxazolidinone

HRID 372341

Reaction equation

HRID 372341 reaction equation
[C:1]([NH2:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[Cl:7][C:8]1[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH:14]=O)=[CH:10][CH:9]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH:14]2[NH:6][C:1](=[O:5])[CH:2]([CH3:4])[O:3]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 94220LactamideHCID 114806982-(4-Chlorophenoxy)acetaldehyde

Product 1

HCID 123914822-(4-Chlorophenoxymethyl)-5-methyl-4-oxazolidinoneYield 2.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

16.9g (0.19 mole) of lactamide was added to a solution containing 32.3g (0.19 mole) of (4-chlorophenoxy)acetaldehyde and 0.2g of p-toluenesulfonic acid in 500 ml of toluene. The mixture was refluxed with stirring for 5 hours while water was removed azeotropically. Toluene was removed under reduced pressure and the residue, which contained at least two major compounds, was purified by silica chromatography to give 1.1g of 2-(4-chlorophenoxymethyl)-5-methyl-4-oxazolidinone, cis isomer, as a white crystalline solid melting at 84°-86°.

Workup

  1. temperatureThe mixture was refluxed
  2. customwas removed azeotropically
  3. customToluene was removed under reduced pressure
  4. customwas purified by silica chromatography

Sources & evidence

ORD record
ord-ba1dec975a65422497b5c031a3cb8d71
Source dataset
uspto-grants-1978_05
Patent number
US04090861

Linked notes

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