Hydrochloric Acid → 3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 1193922

반응식

HRID 1193922 반응식
[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6]CC)=O.[H-].[Na+].[Cl:15][C:16]1[C:21]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][C:19]([N:26]=[C:27]=[O:28])=[C:18]([F:29])[CH:17]=1.Cl>C1(C)C=CC=CC=1.CN(C)C=O.O>[Cl:15][C:16]1[C:21]([O:22][CH:23]([CH3:24])[CH3:25])=[CH:20][C:19]([N:26]2[C:4](=[O:6])[CH:3]=[C:2]([C:9]([F:10])([F:11])[F:12])[NH:1][C:27]2=[O:28])=[C:18]([F:29])[CH:17]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 132729244-Chloro-2-fluoro-5-isopropoxyphenyl isocyanate

생성물 1

HCID 114285773-(4-chloro-2-fluoro-5-isopropoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매2회HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

A solution of 1.0 g of ethyl 3-amino-4,4,4-trifluorocrotonate in 10 ml of absolute toluene is added dropwise while stirring at 0° C. during 15 minutes to a suspension of 0.24 g of a 55% sodium hydride dispersion in 20 ml of absolute dimethylformamide and the mixture is stirred at 0° C. for 15 minutes. The reaction mixture is subsequently cooled to -30° C. and treated with a solution of 1.26 g of 4-chloro-2-fluoro-5-isopropoxyphenyl isocyanate in 10 ml of absolute toluene. The temperature rises rapidly to -10° C. and the reaction mixture is thereafter stirred at room temperature for 2 hours. The reaction mixture is poured into a solution of 3 ml of 2N hydrochloric acid and 500 ml of water and the aqueous mixture is extracted twice with 100 ml of ethyl acetate each time, and the organic phases are washed twice with 50 ml of water each time, dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is recrystalized from diethyl ether/n-hexane. There is obtained 3-(4-chloro-2-fluoro-5-isopropoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, m.p. 195°-197° C.

후처리

  1. temperatureThe reaction mixture is subsequently cooled to -30° C.
  2. customrises rapidly to -10° C.
  3. stirringthe reaction mixture is thereafter stirred at room temperature for 2 hours
  4. extractionthe aqueous mixture is extracted twice with 100 ml of ethyl acetate each time
  5. washthe organic phases are washed twice with 50 ml of water each time
  6. dry with materialdried over anhydrous sodium sulphate
  7. customevaporated to dryness under reduced pressure
  8. customThe residue is recrystalized from diethyl ether/n-hexane

출처 및 근거

ORD 기록
ord-216d22aa144349878c456c1d375ec62f
출처 데이터셋
uspto-grants-1989_03
특허 번호
US04812164

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