Pyridine → isopropyl 2-chloro-5-[2-chloro-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-4-fluorobenzoate

HRID 1193934ノート

反応式

HRID 1193934 の反応式
N1C=CC=CC=1.[Cl:7][C:8]1[CH:19]=[C:18]([F:20])[C:17]([N:21]2[C:26](=[O:27])[CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[NH:23][C:22]2=O)=[CH:16][C:9]=1[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11].P(Cl)(Cl)([Cl:35])=O>C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:19]=[C:18]([F:20])[C:17]([N:21]2[C:26](=[O:27])[CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[N:23]=[C:22]2[Cl:35])=[CH:16][C:9]=1[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11]

参加物

5

反応物 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 19994244isopropyl 2-chloro-5-[3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate

生成物 1

HCID 19994245isopropyl 2-chloro-5-[2-chloro-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-4-fluorobenzoate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

23.3 g of pyridine are added at room temperature while stirring and cooling to a suspension of 38.8 g of isopropyl 2-chloro-5-[3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate in 45.2 g of phosphorus oxychloride and 40 ml of toluene. A solution forms rapidly. The temperature is maintained between 30° to 35° C. and, after 15 minutes, a colourless precipitate begins to separate. The reaction mixture is stirred at 30°-35° C. for 45 minutes and is then poured onto 300 g of ice. The mixture is subsequently extracted with 200 ml of ethyl acetate and the organic phase is washed three times with 50 ml of water each time, dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is recrystallized from n-hexane. There is obtained isopropyl 2-chloro-5-[2-chloro-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-4-fluorobenzoate, m.p. 72°-75° C.

後処理

  1. temperatureThe temperature is maintained between 30° to 35° C. and, after 15 minutes
  2. customto separate
  3. stirringThe reaction mixture is stirred at 30°-35° C. for 45 minutes
  4. additionis then poured onto 300 g of ice
  5. extractionThe mixture is subsequently extracted with 200 ml of ethyl acetate
  6. washthe organic phase is washed three times with 50 ml of water each time
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated to dryness under reduced pressure
  9. customThe residue is recrystallized from n-hexane

出典と根拠

ORDレコード
ord-5ebc755fa9ec45939737f4962484fc3c
出典データセット
uspto-grants-1989_03
特許番号
US04812164

反応ノート

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