3-(Trifluoromethyl)aniline → Talniflumate

HRID 127359노트

반응식

HRID 127359 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].Cl[C:13]1[C:18]([C:19]([O:21][CH:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:24](=[O:25])[O:23]2)=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1>C1(C)C(C)=CC=CC=1>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH:6][C:13]1[C:18]([C:19]([O:21][CH:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:24](=[O:25])[O:23]2)=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1

참가 물질

4

반응물 2

HCID 73753-(Trifluoromethyl)anilineHCID 12673421Phthalidyl 2-chloro-3-pyridinecarboxylate

생성물 1

HCID 48229Talniflumate수율 82.3%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

To 80 ml of xylene, under reflux, m-trifluoromethylaniline (32.2 g) is added. Then, 29 g of phthalidyl 2-chloro-3-pyridinecarboxylate prepared in accordance with Example 1, Supra (divided in two fractions) is poured into the mixture with an interval of 15 minutes between each addition. The reaction mixture so obtained is maintained under reflux for 5 hours, and then cooled by pouring the mixture into an ice/water bath. To allow the complete crystallization of the desired product, the poured reaction mixture is maintained for 2 hours at a temperature of 0°-5° C. The precipitate is collected by filtration and dried under vacuum, at a temperature of 40° C. A yield of 34.1 g (82.3% of theory) of phthalidyl 2-(3-trifluoromethylanilino)-3-pyridinecarboxylate is obtained (m.p. 159°-162° C.). Recrystallizing the compound with 6 volumes of ethyl acetate, 28.4 g (68.5% yield) is obtained (m.p. 164°-5° C.).

후처리

  1. additionis poured into the mixture with an interval of 15 minutes between each addition
  2. customThe reaction mixture so obtained
  3. temperatureis maintained
  4. temperatureunder reflux for 5 hours
  5. temperaturecooled
  6. additionby pouring the mixture into an ice/water bath
  7. customthe complete crystallization of the desired product
  8. customthe poured reaction mixture
  9. temperatureis maintained for 2 hours at a temperature of 0°-5° C
  10. filtrationThe precipitate is collected by filtration
  11. customdried under vacuum, at a temperature of 40° C

출처 및 근거

ORD 기록
ord-30bdcc9f58504e3f887c20d9029bc84a
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04255581

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