2-Hydroxyacetamide → 2-(4-Chloro-2-methylphenoxymethyl)-4-oxazolidinone

HRID 461284

Reaction equation

HRID 461284 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH:8]=[O:9])=[C:4]([CH3:12])[CH:3]=1.[C:13]([NH2:17])(=[O:16])[CH2:14]O>O1CCCC1.CCOCC>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH:8]2[NH:17][C:13](=[O:16])[CH2:14][O:9]2)=[C:4]([CH3:12])[CH:3]=1

Participants

5

Reactant 2

HCID 690212-HydroxyacetamideHCID 123914592-(4-Chloro-2-methylphenoxy)acetaldehyde

Product 1

HCID 123914922-(4-Chloro-2-methylphenoxymethyl)-4-oxazolidinoneYield 18.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution containing 4.6 g (0.025 mole) of (4-chloro-2-methylphenoxy)acetaldehyde and 2.1 g (0.028 mole) of glycolamide in 25 ml of tetrahydrofuran and 25 ml of ether was allowed to stand at ambient temperature for 24 hours. The resulting product was washed with 5% sodium carbonate and water, dried and purified by silica chromatography to give 1.1 g of 2-(4-chloro-2-methylphenoxymethyl)-4-oxazolidinone as a white crystalline solid melting at 109°-112°.

Workup

  1. washThe resulting product was washed with 5% sodium carbonate and water
  2. customdried
  3. custompurified by silica chromatography

Sources & evidence

ORD record
ord-bd0886031fb84779b40d854807ed63a2
Source dataset
uspto-grants-1977_12
Patent number
US04062670

Linked notes

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