Sodium Sulfate → HCID 59421275、化合物

HRID 883004ノート

反応式

HRID 883004 の反応式
[O-:1]S([O-])(=O)=O.[Na+].[Na+].C1C=C(Cl)C=C(C(OO)=O)C=1.[CH2:19]([O:21][C:22]([C:24]1[C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])=[N:26][C:27]([S:30][CH3:31])=[N:28][CH:29]=1)=[O:23])[CH3:20].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:19]([O:21][C:22]([C:24]1[C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])=[N:26][C:27]([S:30]([CH3:31])=[O:1])=[N:28][CH:29]=1)=[O:23])[CH3:20]

参加物

6

反応物 4

HCID 24436Sodium SulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 59421256Ethyl 4-(2-fluorophenyl)-2-(methylthio)-5-pyrimidinecarboxylate

生成物 1

HCID 59421275HCID 59421275、化合物収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A Na2SO4-dried solution of m-CPBA (10.64 g, ca. 45 mmol) in CH2Cl2 (100 mL) was added drop wise to a cold (−65° C.) solution of 4-(2-fluoro-phenyl)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester in CH2Cl2 (200 mL) keeping the temperature below −65° C. The yellow suspension was allowed to warm to 0° C. over 1 hour. After 3 hours at 0° C., a saturated aqueous NaHCO3 solution (100 mL) was added to quench the reaction. The organic layer was separated, washed with saturated aqueous NaCl solution, dried over Na2SO4, and concentrated. The product was taken up in CH2Cl2 and washed again with a saturated aqueous NaHCO3 solution to remove traces of m-C(P)BA giving 4-(2-fluoro-phenyl)-2-methanesulfinyl-pyrimidine-5-carboxylic acid ethyl ester (12.86 g, >100%).

後処理

  1. customthe temperature below −65° C
  2. customto quench
  3. customthe reaction
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaCl solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. washwashed again with a saturated aqueous NaHCO3 solution
  9. customto remove traces

出典と根拠

ORDレコード
ord-f1658885cabb45a3bf6878a5a5ba096e
出典データセット
uspto-grants-2012_08
特許番号
US08236815B2

反応ノート

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