Sodium hydride → HCID 54712966, compound

HRID 1075576Notes

Reaction equation

HRID 1075576 reaction equation
[OH:1][C:2]1[CH2:6][O:5][C:4](=[O:7])[CH:3]=1.[H-].[Na+].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[O:20])=[CH:14][CH:13]=1>O1CCCC1>[F:10][C:11]([F:21])([F:22])[C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19]([C:3]2[C:4](=[O:7])[O:5][CH2:6][C:2]=2[OH:1])=[O:20])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 546838134-Hydroxyfuran-2(5H)-one

Product 1

HCID 54712966HCID 54712966, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-hydroxy-2(5H)-furanone (1.47 g, 14.7 mmol) in tetrahydrofuran (30 ml) was slowly added at 0° C. to a suspension of sodium hydride (80% oil dispersion) (530 mg, 14.7 mmol) in tetrahydrofuran (30 ml). The mixture was stirred at room temperature for 15 minutes, then a solution of 4-trifluoromethylphenyl isocyanate (2.75 g, 14.7 mmol) in tetrahydrofuran (20 ml) was added and the mixture stirred overnight at room temperature. At the end of the reaction, the insoluble product was filtered off and the solvent removed under reduced pressure. Crude product was suspended in water (60 ml) and methanol (6 ml) and the mixture acidified to pH 2 with concentrated HCl; the solid thus obtained was filtered and crystallised from acetone giving 1.75 g (41%) of pure N-(4-trifluoromethylphenyl)-4-hydroxy-2-oxo-(5H)-furan-3-carboxamide as a white solid. m.p.204-206° C. (dec.)

Workup

  1. stirringthe mixture stirred overnight at room temperature
  2. customAt the end of the reaction
  3. filtrationthe insoluble product was filtered off
  4. customthe solvent removed under reduced pressure
  5. customthe solid thus obtained
  6. filtrationwas filtered
  7. customcrystallised from acetone giving 1.75 g (41%) of pure N-(4-trifluoromethylphenyl)-4-hydroxy-2-oxo-(5H)-furan-3-carboxamide as a white solid

Sources & evidence

ORD record
ord-3bbbce40ddd646e588850f7a1252ab3f
Source dataset
uspto-grants-1999_05
Patent number
US05905090

Reaction notes

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