Benzene → thietan-3-yl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoate

HRID 2165799ノート

反応式

HRID 2165799 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]=[C:13]2[O:23][CH3:24])=[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]=[C:13]2[O:23][CH3:24])=[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 197808272-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoic acid

生成物 1

HCID 23042385thietan-3-yl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide触媒

実験手順

3.4 g of 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H) pyrimidinyl]-benzoic acid are heated at reflux temperature for 3 hours in 25 ml of benzene and 3.4 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 1.0 g of 3-thietanol and 1.3 g of pyridine in 20 ml of dioxan. The reaction mixture is then stirred at room temperature for 3.5 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 magnesium sulphate and evaporated. The residue is purified by chromatography on silica gel with diethyl ether/n-hexane (1:2). In this manner there is obtained thietan-3-yl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoate as a colourless oil, 1H-NMR(CDCl3, 400 MHz): 3.37-3.44 (m,2H), 3.57-3.66 (m,2H), 4.03 (s,3H), 5.85 (quintet, 1H), 6.63 (s,1H), 7.42 (d,1H), 7.88 (d,1H).

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 1.0 g of 3-thietanol and 1.3 g of pyridine in 20 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 magnesium sulphate
  8. customevaporated
  9. customThe residue is purified by chromatography on silica gel with diethyl ether/n-hexane (1:2)

出典と根拠

ORDレコード
ord-da537586729049308342174768f40c26
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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