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

HRID 372342

Reaction equation

HRID 372342 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 4.6g (0.025 mole) of (4-chloro-2-methylphenoxy)acetaldehyde and 2.1g (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 1.1g 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-2005a2a0641041d69c36b39cd9a7f613
Source dataset
uspto-grants-1978_05
Patent number
US04090861

Linked notes

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