Ethanol → HCID 18770550, compound

HRID 479488Notes

Reaction equation

HRID 479488 reaction equation
O1[CH2:5][CH2:4][NH:3]C1=O.[ClH:7].[F:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12].C(O)C>C(OCC)C>[ClH:7].[F:8][C:9]1[CH:10]=[C:11]([NH:12][CH2:5][CH2:4][NH2:3])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 739492-OxazolidinoneHCID 27557653-Fluorophenylamine hydrochloride

Product 1

HCID 18770550HCID 18770550, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
165 °C

Procedure

Equimolar quantities (45.7 mmol) of 2-oxazolidinone and 3-fluoroaniline hydrochloride were combined, heated to 165° C., and stirred for 18 hours. The dark-colored mixture was allowed to cool to ambient temperature and treated with ethanol (125 mL). The suspension was heated to reflux for 1 hour, allowed to cool to ambient temperature, treated with diethyl ether (125 mL), and the suspension was cooled to 0° C. for 2 hours. Filtration provided 5.53 g of the desired product as colorless crystals which were used without further purification.

Workup

  1. temperatureto cool to ambient temperature
  2. temperatureThe suspension was heated
  3. temperatureto reflux for 1 hour
  4. temperatureto cool to ambient temperature
  5. temperaturethe suspension was cooled to 0° C. for 2 hours
  6. filtrationFiltration

Sources & evidence

ORD record
ord-a6a0b2b8b8a94cf7962a2231c94cf5d5
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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