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

HRID 1585222
노트
인쇄 미리보기

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HRID 1585222 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6212
Chloroform
용매

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온도
-78 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c784762be53945f4b205831ac9709604
출처 데이터셋
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05936098

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