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

HRID 342687

반응식

HRID 342687 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-29bb2f0d30554742bb809c953a2bc56e
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859041

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