Ethyl 3-amino-4,4,4-trifluorocrotonate → 3-(4-Bromo-5-ethoxy-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 566183노트

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HRID 566183 반응식
[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6]CC)=O.C[O-].[Na+].[Br:16][C:17]1[C:22]([O:23][CH2:24][CH3:25])=[CH:21][C:20]([NH:26][C:27](=O)[O:28]CC)=[C:19]([F:32])[CH:18]=1>CN(C=O)C>[Br:16][C:17]1[C:22]([O:23][CH2:24][CH3:25])=[CH:21][C:20]([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:19]([F:32])[CH:18]=1

참가 물질

5

반응물 3

HCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 10942334Sodium MethoxideHCID 21265588ethyl N-(4-bromo-5-ethoxy-2-fluorophenyl)carbamate

생성물 1

HCID 212655333-(4-Bromo-5-ethoxy-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

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온도
5 °C

실험 절차

Ethyl 3-amino-4,4,4-trifluorocrotonate (3.42 g) was dissolved in DMF (19 ml). To this solution, a suspension of sodium methoxide (1.10 g) in DMF was added dropwise at 5° C., and the mixture was stirred at 5° C. for 30 minutes. Then, a DNF solution of ethyl N-(4-bromo-5-ethoxy-2-fluorophenyl)-carbamate was added dropwise thereto, and the mixture was stirred at 130° C. for 4 hours. After the reaction, DMF was distilled off under reduced pressure. Then, the residue was acidified by adding diluted hydrochloric acid thereto. This was extracted with ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off, and the resulting residue was crystallized from a mixed solvent of ethyl acetate and n-hexane (1:3 v/v) to obtain the objective 3-(4-bromo-5-ethoxy-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (3.63 g).

후처리

  1. additionwas added dropwise at 5° C.
  2. stirringthe mixture was stirred at 130° C. for 4 hours
  3. distillationwas distilled off under reduced pressure
  4. additionby adding diluted hydrochloric acid
  5. extractionThis was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThen, ethyl acetate was distilled off
  9. customthe resulting residue was crystallized from a mixed solvent of ethyl acetate and n-hexane (1:3 v/v)

출처 및 근거

ORD 기록
ord-0d8681e32826420da7d49e8f21226107
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06174839B1

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