Chloride → HCID 67313482、化合物

HRID 1391499ノート

反応式

HRID 1391499 の反応式
[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]

参加物

7

反応物 4

HCID 312ChlorideHCID 516892Sodium Bicarbonate2 回HCID 2799903HCID 2799903、化合物HCID 67313799HCID 67313799、化合物

生成物 1

HCID 67313482HCID 67313482、化合物収率 84%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 3776Isopropanol溶媒

反応条件

温度
55 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-09ef2f048b974ae191c4136b17f9317b
出典データセット
uspto-grants-2008_03
特許番号
US07338967B2

反応ノート

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