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Boron tribromide → N-{2-Hydroxy-5-[2-(3-propyl-[1,2,4]oxadiazol-5-yl)-vinyl]-phenyl}-methanesulfonamide

HRID 470614
ノート
印刷プレビュー

反応式

HRID 470614 の反応式
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[O:15][N:14]=[C:13]([CH2:16][CH2:17][CH3:18])[N:12]=2)=[CH:5][C:4]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[O:15][N:14]=[C:13]([CH2:16][CH2:17][CH3:18])[N:12]=2)=[CH:5][C:4]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 67396842N-{2-Methoxy-5-[2-(3-propyl-[1,2,4]oxadiazol-5-yl)-vinyl]-phenyl}-methane sulfonamide2 回

生成物 1

HCID 136413212N-{2-Hydroxy-5-[2-(3-propyl-[1,2,4]oxadiazol-5-yl)-vinyl]-phenyl}-methanesulfonamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

N-{2-Methoxy-5-[2-(3-propyl-[1,2,4]oxadiazol-5-yl)-vinyl]-phenyl}-methane sulfonamide (compound of Example 9; 0.08 g, 0.23 mmol) was dissolved in dichloromethane (7 mL) and cooled to −78° C. A solution of boron tribromide in dichloromethane (0.15 mL, 1.61 mmol) was cooled to −78° C. and slowly added to the reaction mixture. After 1.5 h, the reaction mixture was warmed to room temperature and stirred for 3 h. At the end of 3 h, the mixture was quenched by dropwise addition of methanol (5 mL) at 0° C. and stirred for 20 min at room temperature. The solvent was evaporated, and the residue was redissolved in a mixture of 10% methanol in chloroform at 0° C. Solid sodium carbonate was added to this solution to adjust pH to 8. The solvent was evaporated and the crude product obtained was purified by column chromatography (silica gel, 0.5% methanol in chloroform) to afford the title compound.

後処理

  1. additionslowly added to the reaction mixture
  2. temperaturethe reaction mixture was warmed to room temperature
  3. customAt the end of 3 h, the mixture was quenched by dropwise addition of methanol (5 mL) at 0° C.
  4. stirringstirred for 20 min at room temperature
  5. customThe solvent was evaporated
  6. dissolutionthe residue was redissolved in a mixture of 10% methanol in chloroform at 0° C
  7. additionSolid sodium carbonate was added to this solution
  8. customThe solvent was evaporated
  9. customthe crude product obtained
  10. customwas purified by column chromatography (silica gel, 0.5% methanol in chloroform)

出典と根拠

ORDレコード
ord-7b349e5241fa4106aeb1ab795e114c3c
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08629277B2

反応ノート

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