Sulfuric Acid → 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoic acid

HRID 2165805ノート

反応式

HRID 2165805 の反応式
[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]=[C:16]2[O:26][CH3:27])=[CH:10][C:3]=1[C:4]([O:6]C(C)C)=[O:5].S(=O)(=O)(O)O>C(Cl)Cl>[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:23])([F:25])[F:24])[N:17]=[C:16]2[O:26][CH3:27])=[CH:10][C:3]=1[C:4]([OH:6])=[O:5]

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 19994237isopropyl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoate

生成物 1

HCID 197808272-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 5 g of isopropyl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H) pyrimidinyl]-benzoate in 20 ml of methylene chloride is treated with 25 ml of concentrated sulphuric acid while stirring and cooling at 20°-25° C. The reaction mixture is stirred at room temperature for a further 20 minutes and poured on to 100 g of ice. The organic phase is separated, the aqueous phase is extracted twice with 15 ml of ethyl acetate each time and the combined organic phases are washed to neutrality with water. The solution is subsequently dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The resinous residue is recrystallized from diethyl ether/n-hexane. There is obtained 2-chloro-4-fluoro-5-[2 -methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoic acid, m.p. 205°-210° C.

後処理

  1. temperaturecooling at 20°-25° C
  2. stirringThe reaction mixture is stirred at room temperature for a further 20 minutes
  3. customThe organic phase is separated
  4. extractionthe aqueous phase is extracted twice with 15 ml of ethyl acetate each time
  5. washthe combined organic phases are washed
  6. dry with materialThe solution is subsequently dried over anhydrous sodium sulphate
  7. customevaporated to dryness under reduced pressure
  8. customThe resinous residue is recrystallized from diethyl ether/n-hexane

出典と根拠

ORDレコード
ord-6e70e8d66f124aaabadcf8256cb1e790
出典データセット
uspto-grants-1990_07
特許番号
US04941909

反応ノート

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