Sodium Bicarbonate → HCID 59759989、化合物

HRID 1672416ノート

反応式

HRID 1672416 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][CH:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[OH:23].C(=O)(O)[O-].[Na+]>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[CH:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[OH:23]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 2799903HCID 2799903、化合物HCID 67313359HCID 67313359、化合物

生成物 1

HCID 59759989HCID 59759989、化合物収率 16.7%

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 52 mg (0.23 mmol) of 2,4-dichloro-N-hydroxybenzenecarboximidoyl chloride, 50 mg (0.21 mmol) of 3-(2-chlorophenyl)-1-(3-pyridyl)-2-propyn-1-ol, and 30 mg (0.36 mmol) of sodium bicarbonate in 3 mL of isopropyl alcohol was heated at 55° C. overnight with shaking. 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 15 mg (0.035 mmol) of 5-(2-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)hydroxymethyl]isoxazole. 1H NMR (CDCl3): δ 5.80 (br s, 1). MS m/z: 431.0 (M+H).

後処理

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

出典と根拠

ORDレコード
ord-787d486783404ee9b1d2b3520fab7823
出典データセット
uspto-grants-2011_08
特許番号
US07998983B2

反応ノート

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