Potassium Carbonate → 5,5-Dimethyl-[(4-methoxy-6-trifluoromethylpyrimidin-5-yl)-methylthio]-2-isoxazoline

HRID 1172086ノート

反応式

HRID 1172086 の反応式
[SH-].[Na+].[CH3:3][C:4]1([CH3:13])[O:8][N:7]=[C:6]([S:9]([CH3:12])(=O)=O)[CH2:5]1.C(=O)([O-])[O-].[K+].[K+].C(S([O-])=O)O.[Na+].ClC[C:28]1[C:29]([O:38][CH3:39])=[N:30][CH:31]=[N:32][C:33]=1[C:34]([F:37])([F:36])[F:35]>CN(C)C=O.O>[CH3:3][C:4]1([CH3:13])[O:8][N:7]=[C:6]([S:9][CH2:12][C:28]2[C:29]([O:38][CH3:39])=[N:30][CH:31]=[N:32][C:33]=2[C:34]([F:36])([F:37])[F:35])[CH2:5]1

参加物

8

反応物 5

HCID 11430Potassium CarbonateHCID 28015Sodium hydrosulfideHCID 121376563-Methylsulfonyl-5,5-dimethyl-2-isoxazolineHCID 178629155-Chloromethyl-4-methoxy-6-trifluoromethylpyrimidineHCID 23689980Sodium Formaldehyde Sulfoxylate

生成物 1

HCID 686218485,5-Dimethyl-[(4-methoxy-6-trifluoromethylpyrimidin-5-yl)-methylthio]-2-isoxazoline収率 85.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

0.32 g of sodium hydrosulfide (purity: 70%, 4.00 mmoles) was added, at room temperature, to a solution of 0.35 g (2.00 mmoles) of 5,5-dimethyl-3-methylsulfonyl-2-isoxazoline dissolved in 10 ml of dimethylformamide. The mixture was stirred for 2 hours. To the reaction mixture were added 0.28 g (2.00 mmoles) of anhydrous potassium carbonate, 0.31 g (2.00 mmoles) of Rongalit and 0.45 g (2.00 mmoles) of 5-chloromethyl-4-methoxy-6-trifluoromethylpyrimidine. The resulting mixture was stirred at room temperature for 2 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The resulting organic layer was washed with water and an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography to obtain 0.55 g (yield: 85.9%) of 5,5-dimethyl-[(4-methoxy-6-trifluoromethylpyrimidin-5-yl)-methylthio]-2-isoxazoline.

後処理

  1. stirringThe resulting mixture was stirred at room temperature for 2 hours
  2. customto give rise
  3. customto a reaction
  4. customAfter confirmation of the completion of the reaction
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe resulting organic layer was washed with water
  7. dry with materialan aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate
  8. distillationThe resulting solution was subjected to vacuum distillation
  9. customto remove the solvent
  10. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-618803e3eec44122a420546ba9148e2f
出典データセット
uspto-grants-2010_11
特許番号
US07833939B2

反応ノート

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