Hydrochloric Acid → 3-[4-chloro-5-(2-chloro-1,1,2-trifluoroethoxy)-2-fluorophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 1722978

反応式

HRID 1722978 の反応式
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([F:22])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:29][C:30]([F:34])=[C:31]([F:33])[F:32].Cl>O>[Cl:1][C:2]1[C:7]([O:8][C:31]([F:33])([F:32])[CH:30]([Cl:29])[F:34])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([F:22])[CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6594Chlorotrifluoroethylene2 回HCID 11430Potassium CarbonateHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

生成物 1

HCID 200261363-[4-chloro-5-(2-chloro-1,1,2-trifluoroethoxy)-2-fluorophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of 2.0 g of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6 -trifluoromethyl-2,4(1H,3H)pyrimidinedione is treated with 0.25 g of potassium carbonate and the suspension is saturated with chlorotrifluoroethylene while stirring during 10 minutes. The reaction mixture is subsequently heated to 50° C. for 10 minutes, during which a slow stream of chlorotrifluoroethylene is conducted in. Thereafter, the reaction mixture is poured into a solution of 3 ml of 2N hydrochloric acid in 250 ml of water, and the whole is extracted with 100 ml of ethyl acetate. The organic phase is washed neutral with water, dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The resinous residue is purified by chromatography on a silica gel column using diethyl ether/n-hexane (1:3) as the eluent. There is obtained 3-[4-chloro-5-(2-chloro-1,1,2-trifluoroethoxy)-2-fluorophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, 1H-NMR (CDCl3, 400 MHz : 7.40 ppm (d,1H), 7.32 ppm (m,1H), 6.37 ppm (s,1H), 6.33 ppm (m,1H), 3.57 ppm (d,3H).

後処理

  1. extractionthe whole is extracted with 100 ml of ethyl acetate
  2. washThe organic phase is washed neutral with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated to dryness under reduced pressure
  5. customThe resinous residue is purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-c2ab1cf2a89e4a5bac93d78dc6873dac
出典データセット
uspto-grants-1989_08
特許番号
US04859229

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