Chloride → HCID 67313482, 화합물

HRID 1010698노트

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HRID 1010698 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](Cl)=[N:10][OH:11].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]#[C:21][C:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:23].C(=O)(O)[O-].[Na+].[Cl-]>C(O)(C)C.CCOCC>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[O:11][N:10]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[C:21]=1[C:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:23]

참가 물질

7

반응물 4

HCID 312ChlorideHCID 516892Sodium Bicarbonate2회HCID 2799903HCID 2799903, 화합물HCID 67313799HCID 67313799, 화합물

생성물 1

HCID 67313482HCID 67313482, 화합물수율 84%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 3776Isopropanol용매

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온도
55 °C

실험 절차

A mixture of 56 mg (0.25 mmol) of 2,4-dichloro-N-hydroxybenzenecarboximidoyl chloride, 60 mg (0.25 mmol) of 3-(2-chlorophenyl)-1-(3-pyridyl)-2-propyn-1-one, and 30 mg (0.36 mmol) of sodium bicarbonate in 2.5 mL of isopropyl alcohol was heated at 55° C. overnight with shaking. An additional 30 mg of carboximidoyl chloride and 15 mg of sodium bicarbonate was then added, and the mixture was heated for another 20 hrs. The reaction mixture was cooled, diluted with ether, and then washed with saturated sodium bicarbonate. The ether fraction was dried over magnesium sulfate. The drying agent was filtered off, and the ether was removed by rotoevaporation. The crude product was purified by prep TLC to give 90 mg (0.21 mmol) of 5-(2-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)carbonyl]isoxazole. 1H NMR (CDCl3): δ 7.16 (m, 1), 7.60 (m, 2), 7.92 (m, 1), 8.53 (br d, 1), and 8.74 ppm (br s, 1). MS m/z: 428.9 (M+H).

후처리

  1. temperaturethe mixture was heated for another 20 hrs
  2. temperatureThe reaction mixture was cooled
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialThe ether fraction was dried over magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe ether was removed by rotoevaporation
  7. customThe crude product was purified by prep TLC

출처 및 근거

ORD 기록
ord-5b76fea7ce0d46259b6202865e82403b
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977341B2

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