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Hydrochloric Acid → 2-(4-((5-Chloro-3-fluoro-2-pyridinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide

HRID 1655544
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HRID 1655544 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([F:21])[C:5]([O:8][C:9]2[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15](Cl)=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.Cl.[F:23][C:24]([F:34])([F:33])[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.N1C=CC=CC=1.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([F:21])[C:5]([O:8][C:9]2[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15]([NH:30][C:29]3[CH:31]=[CH:32][C:26]([O:25][C:24]([F:23])([F:33])[F:34])=[CH:27][CH:28]=3)=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 27810604-(trifluoromethoxy)aniline HydrochlorideHCID 197926722-[4-(5-Chloro-3-fluoropyridin-2-yloxy)phenoxy]propionyl chloride

생성물 1

HCID 197926782-(4-((5-Chloro-3-fluoro-2-pyridinyl)oxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide수율 15%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 4.8 mmol of 2-(4-((5-chloro-3-fluoro-2-pyridinyl)oxy)phenoxy)propanoyl chloride (previously prepared from the corresponding acid) in 15 ml of methylene chloride was added, under N2, to an ice-cooled mixture of 1.03 g (4.8 mmol) of 4-(trifluoromethoxy)aniline hydrochloride, 0.95 g (12 mmol) of pyridine and 25 ml of methylene chloride. The resulting mixture was stirred at ambient temperature overnight and then poured into dilute aqueous HCl. The aqueous layer was separated and extracted with CH2Cl2. The combined organic layers were washed twice with saturated aqueous sodium bicarbonate, treated with charcoal and MgSO4 and filtered. The filtrates were evaporated to dryness and the residue recrystallized from methylcyclohexane to give 0.34 g of the above-named product as colorless crystals, m.p. 92°-93.5° C. (Compound 37)

후처리

  1. temperaturecooled
  2. customThe aqueous layer was separated
  3. extractionextracted with CH2Cl2
  4. washThe combined organic layers were washed twice with saturated aqueous sodium bicarbonate
  5. additiontreated with charcoal and MgSO4
  6. filtrationfiltered
  7. customThe filtrates were evaporated to dryness
  8. customthe residue recrystallized from methylcyclohexane

출처 및 근거

ORD 기록
ord-d765d128b5754ab9a36f3c5abf389291
출처 데이터셋
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05250690

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