Pyridine → 2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorophenyl chlorosulphate

HRID 1722975

反応式

HRID 1722975 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.[S:23](Cl)([Cl:26])(=[O:25])=[O:24].N1C=CC=CC=1>C(Cl)Cl>[S:23]([Cl:26])([O:8][C:7]1[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][C:2]=1[Cl:1])(=[O:25])=[O:24]

参加物

5

反応物 3

HCID 1049PyridineHCID 24648Sulfuryl chlorideHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

生成物 1

HCID 200260872-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorophenyl chlorosulphate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 10.16 g of 3-(4-chloro-2-fluoro-5 -hydroxyphenyl)-1-methyl-6 -trifluoromethyl-2,4 (1H,3H)-pyrimidinedione and 20.20 g of sulphuryl chloride in 100 ml of methylene chloride is treated with a solution of 3.56 g of pyridine in 10 ml of methylene chloride while stirring and cooling during 5 minutes. The temperature rises to 20° C. The reaction mixture is stirred at 20°-25° C. for 15 minutes, subsequently poured on to ice and stirred vigorously. The organic phase is washed throughly with water, dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is recrystallized from diethyl ether/n-hexane. There is obtained 2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorophenyl chlorosulphate m.p. 133°-135° C.

後処理

  1. temperaturecooling during 5 minutes
  2. customrises to 20° C
  3. stirringThe reaction mixture is stirred at 20°-25° C. for 15 minutes
  4. additionsubsequently poured on to ice
  5. stirringstirred vigorously
  6. washThe organic phase is washed throughly with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated to dryness under reduced pressure
  9. customThe residue is recrystallized from diethyl ether/n-hexane

出典と根拠

ORDレコード
ord-022611f6d05d4297949c64fd8b8d2105
出典データセット
uspto-grants-1989_08
特許番号
US04859229

関連ノート

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