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

HRID 1722975

반응식

HRID 1722975 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-022611f6d05d4297949c64fd8b8d2105
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04859229

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