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Dichloromethane → 5-[3-(3-Hydroxyphenyl)indolin-1-ylcarbonyl]-4,5,6,7-tetrahydrobenzimidazole

HRID 1585222
ノート
印刷プレビュー

反応式

HRID 1585222 の反応式
C[O:2][C:3]1[CH:4]=[C:5]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([C:18]([CH:20]3[CH2:28][CH2:27][C:23]4[N:24]=[CH:25][NH:26][C:22]=4[CH2:21]3)=[O:19])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1.ClCCl.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([C:18]([CH:20]3[CH2:28][CH2:27][C:23]4[N:24]=[CH:25][NH:26][C:22]=4[CH2:21]3)=[O:19])[CH2:10]2)[CH:6]=[CH:7][CH:8]=1
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

6

反応物 4

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 212222825-[3-(3-Methoxyphenyl)indolin-1-ylcarbonyl]-4,5,6,7-tetrahydrobenzimidazole

生成物 1

HCID 99287795-[3-(3-Hydroxyphenyl)indolin-1-ylcarbonyl]-4,5,6,7-tetrahydrobenzimidazole収率 76.1%

試薬・触媒・溶媒 1

HCID 6212
Chloroform
溶媒

反応条件

温度
-78 °C

実験手順

In 9 ml of chloroform, 300 mg of the optically active 5-[3-(3-methoxyphenyl]indolin-1-ylcarbonyl!-4,5,6,7-tetrahydrobenzimidazole obtained in Example 24 was solved. This solution and 3.1 ml of a 1.0M dichloromethane solution of boron tribromide added thereto in a stream of argon at -78° C. were together stirred at -78° C. for three hours and further at normal room temperature for three hours. The resultant reaction solution was poured into ice water, neutralized with an aqueous sodium hydrogen carbonate solution, and then extracted with a mixed solution of chloroform and ethanol. The organic layer was dried over magnesium sulfate and then distilled. The residue of the distillation was refined by silica gel column chromatography to obtain 220 mg of optically active 5-[3-(3-hydroxyphenyl)indolin-1-ylcarbonyl]-4,5,6,7-tetrahydrobenzimidazole (76.1%).

後処理

  1. customThe resultant reaction solution
  2. extractionextracted with a mixed solution of chloroform and ethanol
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. distillationdistilled
  5. distillationThe residue of the distillation

出典と根拠

ORDレコード
ord-c784762be53945f4b205831ac9709604
出典データセット
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05936098

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート