Carbanilide → HCID 10130204, compound

HRID 650260Notes

Reaction equation

HRID 650260 reaction equation
C1(N[C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])C=CC=CC=1.[F-].[Cs+].[CH3:19][CH:20]1[CH2:24]OC(=O)[O:21]1>CS(C)=O>[C:11]1([N:10]2[CH2:19][CH:20]([CH3:24])[O:21][C:8]2=[O:9])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 7595CarbanilideHCID 7924Propylene CarbonateHCID 25953Cesium fluoride

Product 1

HCID 10130204HCID 10130204, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

N,N′-Diphenylurea (20.7 g, 98.0 mmol) was dissolved in dimethyl sulfoxide (40 mL), and thereto were added cesium fluoride (1.48 g, 9.80 mmol) and 4-methyl-1,3-dioxolan-2-one (10.0 g, 98.0 mmol), in order. The mixture was stirred for 30 hours at 140° C. under an atmosphere of argon. After filtering off the insoluble materials, the filtrate was condensed in vacuo, and the residue was recrystallized from ethanol to give the subject 3-phenyl-5-methyloxazolidin-2-one (12.9 g, yield 74.3%).

Workup

  1. filtrationAfter filtering off the insoluble materials
  2. customcondensed in vacuo
  3. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-96b9886ec270433693ba5ba05ada4c7e
Source dataset
uspto-grants-2001_08
Patent number
US06271388B1

Reaction notes

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