Benzene → thietan-3-yl 2-chloro-5-[3,6-dihydro-2 6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate

HRID 2165796ノート

反応式

HRID 2165796 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[S:25](Cl)(Cl)=O.[CH:29]1[CH:34]=CC=C[CH:30]=1>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:21])([F:20])[F:22])[N:14]([CH3:23])[C:13]2=[O:24])=[CH:7][C:3]=1[C:4]([O:6][CH:29]1[CH2:34][S:25][CH2:30]1)=[O:5]

参加物

5

反応物 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 120567892-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoic acid

生成物 1

HCID 23042363thietan-3-yl 2-chloro-5-[3,6-dihydro-2 6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide触媒

実験手順

3.0 g of 2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoic acid are heated at reflux temperature for 3 hours in 20 ml of benzene and 2.9 ml of thionyl chloride together with 2 drops of dimethylformamide. The reaction mixture is subsequently evaporated to dryness and dissolved in 20 ml of dioxan. This solution, which consists mainly of the acid chloride of the above-mentioned benzoic acid and the solvent, is added dropwise to a solution of 0.86 g of 3-thietanol and 1.0 g of pyridine in 10 ml of dioxan. The reaction mixture is then stirred at room temperature for 2.5 hours, treated with 400 ml of water and extracted twice with 400 ml of ethyl acetate each time. The combined organic phases are washed twice with 200 ml of 1N hydrochloric acid each time and once with 200 ml of saturated sodium chloride solution, dried over anhydrous sodium sulphate and evaporated. The residue is purified by chromatography on silica gel with ethyl acetate/n-hexane (2:3). In this manner there is obtained thietan-3-yl 2-chloro-5-[3,6-dihydro-2 6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate which can be recrystallized from ethyl acetate/n-hexane; m.p. 121°-123° C.

後処理

  1. customThe reaction mixture is subsequently evaporated to dryness
  2. dissolutiondissolved in 20 ml of dioxan
  3. additionthe solvent, is added dropwise to a solution of 0.86 g of 3-thietanol and 1.0 g of pyridine in 10 ml of dioxan
  4. additiontreated with 400 ml of water
  5. extractionextracted twice with 400 ml of ethyl acetate each time
  6. washThe combined organic phases are washed twice with 200 ml of 1N hydrochloric acid each time
  7. dry with materialonce with 200 ml of saturated sodium chloride solution, dried over anhydrous sodium sulphate
  8. customevaporated
  9. customThe residue is purified by chromatography on silica gel with ethyl acetate/n-hexane (2:3)

出典と根拠

ORDレコード
ord-a9732dfc9f6f4d8fac8c2d0b8f9a04c6
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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