Potassium Carbonate → 3-(4-Ethoxy-6-trifluoromethylpyrimidin-5-ylmethylthio)-5-chloromethyl-5-methyl-2-isoxazoline

HRID 254204ノート

反応式

HRID 254204 の反応式
O.[SH-].[Na+].[CH3:4][S:5]([C:8]1[CH2:12][C:11]([CH2:14][Cl:15])([CH3:13])[O:10][N:9]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].C(S([O-])=O)O.[Na+].BrC[C:30]1[C:31]([O:40][CH2:41][CH3:42])=[N:32][CH:33]=[N:34][C:35]=1[C:36]([F:39])([F:38])[F:37]>CN(C=O)C.C(OCC)(=O)C.O>[CH2:41]([O:40][C:31]1[C:30]([CH2:4][S:5][C:8]2[CH2:12][C:11]([CH2:14][Cl:15])([CH3:13])[O:10][N:9]=2)=[C:35]([C:36]([F:38])([F:39])[F:37])[N:34]=[CH:33][N:32]=1)[CH3:42]

参加物

9

反応物 5

HCID 11430Potassium CarbonateHCID 111952063-Methylsulfonyl-5-chloromethyl-5-methyl-2-isoxazolineHCID 16211346Sodium hydrosulfide hydrateHCID 178628575-Bromomethyl-4-ethoxy-6-trifluoromethylpyrimidineHCID 23689980Sodium Formaldehyde Sulfoxylate

生成物 1

HCID 229348943-(4-Ethoxy-6-trifluoromethylpyrimidin-5-ylmethylthio)-5-chloromethyl-5-methyl-2-isoxazoline収率 30.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3.4 g (42.3 mmoles) of sodium hydrosulfide hydrate (purity: 70%) was added into a solution of 4.6 g (21.6 mmoles) of 3-methylsulfonyl-5-chloromethyl-5-methyl-2-isoxazoline dissolved in 70 ml of DMF. The mixture was stirred for 2 hours. Then, there were added 3.0 g (21.6 mmoles) of potassium carbonate, 3.3 g (21.6 mmoles) of Rongalit and 5-bromomethyl-4-ethoxy-6-trifluoromethylpyrimidine. The mixture was stirred at room temperature for 21 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water and extraction with ethyl acetate was conducted. The resulting organic layer was washed with an aqueous sodium chloride solution, followed by drying over anhydrous magnesium sulfate. The resulting solution was subjected to reduced pressure distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (solvent system: hexane-ethyl acetate) to obtain 1.9 g (yield: 30.3%) of 3-(4-ethoxy-6-trifluoromethylpyrimidin-5-ylmethylthio)-5-chloromethyl-5-methyl-2-isoxazoline.

後処理

  1. stirringThe mixture was stirred at room temperature for 21 hours
  2. customto give rise
  3. customto a reaction
  4. customAfter the completion of the reaction
  5. washThe resulting organic layer was washed with an aqueous sodium chloride solution
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. distillationThe resulting solution was subjected to reduced pressure distillation
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography (solvent system: hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-9c5e06a7a55f4f6baaa213ad8b2a5e04
出典データセット
uspto-grants-2011_01
特許番号
US07875606B2

反応ノート

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