Water → 2-Chloro-4-fluoro-5-(6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)benzaldehyde (O-methyl)oxime

HRID 566600노트

반응식

HRID 566600 반응식
[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6]CC)=O.[H-].[Na+].[CH3:15][O:16][N:17]=[CH:18][C:19]1[CH:24]=[C:23]([N:25]=[C:26]=[O:27])[C:22]([F:28])=[CH:21][C:20]=1[Cl:29].O>CN(C)C=O.O1CCCC1.ClCCl>[CH3:15][O:16][N:17]=[CH:18][C:19]1[CH:24]=[C:23]([N:25]2[C:4](=[O:6])[CH:3]=[C:2]([C:9]([F:10])([F:11])[F:12])[NH:1][C:26]2=[O:27])[C:22]([F:28])=[CH:21][C:20]=1[Cl:29]

참가 물질

8

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 542049932-Chloro-4-fluoro-5-isocyanatobenzaldehyde (O-methyl)oxime

생성물 1

HCID 570273782-Chloro-4-fluoro-5-(6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)benzaldehyde (O-methyl)oxime

시약·촉매·용매 3

HCID 6228Dimethylformamide용매2회HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
20 °C

실험 절차

A solution of 168.5 g (0.92 mol) of ethyl 3-amino-4,4,4-trifluorocrotonate in 0.1 l of dimethylformamide was added dropwise with ice-cooling to 30.4 g (1.01 mol) of 80% by weight sodium hydride in 0.5 l of dimethylformamide. After one hour at this temperature, the mixture was cooled to (−30) to (−35)° C., and a solution of 210.3 g (0.92 mol) of 2-chloro-4-fluoro-5-isocyanatobenzaldehyde (O-methyl)oxime in 0.15 l of tetrahydrofuran was added dropwise. The reaction mixture was then stirred for 20 hours at approximately 20° C., and 1.5 l of water were subsequently added with ice-cooling. Undissolved matter in the mixture formed was removed and washed using 300 ml of water. The combined filtrates were acidified using dilute hydrochloric acid. The product of value was then extracted from the solution obtained using dichloromethane. The extract was washed with water, dried over sodium sulfate and finally concentrated. Yield: 289 g; m.p.: 176-177° C. (diisopropyl ether/petroleum ether).

후처리

  1. temperaturecooling
  2. customUndissolved matter in the mixture formed
  3. customwas removed
  4. washwashed
  5. extractionThe product of value was then extracted from the solution
  6. customobtained
  7. washThe extract was washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationfinally concentrated

출처 및 근거

ORD 기록
ord-f45abe62a40e43639a860c920e30e445
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06175007B1

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