Tetrahydrofuran → 1-(2-Methylthiopyrimidin-4-yl)-2-(3-trifluoromethylphenyl)ethane-1,2-dione-1-oxime

HRID 342687Notes

Reaction equation

HRID 342687 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[O:11])[CH:6]=[CH:5][N:4]=1.C1COCC1.[N:27]([O-])=[O:28].[Na+].[OH-].[Na+]>C(O)(=O)C.O.C(OCC)(=O)C>[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9](=[N:27][OH:28])[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=2)=[O:11])[CH:6]=[CH:5][N:4]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 107574582-[2-(Methylthio)pyrimidin-4-yl]-1-[3-(trifluoromethyl)phenyl]ethanoneHCID 23668193Sodium Nitrite

Product 1

HCID 1363653261-(2-Methylthiopyrimidin-4-yl)-2-(3-trifluoromethylphenyl)ethane-1,2-dione-1-oxime

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(2-methylthiopyrimidin-4-yl)-1-(3-trifluoromethylphenyl)ethanone (4.5 g, 0.0144 mole) in acetic acid (67 mL), was added THF (54 mL) and water (9 mL). The mixture was cooled to +5° C. and a solution of sodium nitrite (1.34 g, 0.0194 mole) added dropwise while maintaining the temperature below +10° C. Upon completion of addition, the reaction was allowed to warm to room temperature for 1 hour, diluted with water (200 mL) and ethyl acetate (200 mL) and the pH adjusted to 7.5 with 3N NaOH. The layers were separated and the aqueous layer washed with ethyl acetate (100 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated to an oil. Yield 4.9 g.

Workup

  1. temperatureThe mixture was cooled to +5° C.
  2. temperaturewhile maintaining the temperature below +10° C
  3. additionUpon completion of addition
  4. customThe layers were separated
  5. washthe aqueous layer washed with ethyl acetate (100 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-29bb2f0d30554742bb809c953a2bc56e
Source dataset
uspto-grants-1999_01
Patent number
US05859041

Reaction notes

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