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

HRID 1585222
Notes
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Reaction equation

HRID 1585222 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-78 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-c784762be53945f4b205831ac9709604
Source dataset
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05936098

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes