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

HRID 342687ノート

反応式

HRID 342687 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-29bb2f0d30554742bb809c953a2bc56e
出典データセット
uspto-grants-1999_01
特許番号
US05859041

反応ノート

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