Hydrazine hydrate (1:1) → HCID 19600385, compound

HRID 609768Notes

Reaction equation

HRID 609768 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:18]([NH:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH2:30][CH2:31][CH2:32][N:33]1C(=O)C3=CC=CC=C3C1=O)[CH:25]=[CH:24]2)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:18]([NH:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH2:30][CH2:31][CH2:32][NH2:33])[CH:25]=[CH:24]2)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19600381HCID 19600381, compound

Product 1

HCID 19600385HCID 19600385, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 5 g of 1-benzyl-6-chloro-2-[1-(3-phthalimidopropyl)indol-5-ylaminocarbonyl]benzimidazole was added 100 ml of ethanol and stirred, then 0.5 ml of hydrazine hydrate was added thereto, the mixture was refluxed overnight. After cooled the reaction mixture to room temperature, then white crystals were removed by filtration. Water was added to the filtrate, and made alkaline with 10% aqueous solution of potassium hydroxide. This mixture was extracted with dichloromethane, the extract was washed with water, an aqueous solution saturated with sodium chloride then was dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was crystallized from ethyl acetate-n-hexane, there was obtained 3.2 g of 1-benzyl-6-chloro-2-[1-(3-aminopropyl)indol-5-ylaminocarbonyl]-benzimidazole as in the form of yellow granular crystals. Melting point: 106-108° C.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customwhite crystals were removed by filtration
  3. additionWater was added to the filtrate
  4. extractionThis mixture was extracted with dichloromethane
  5. washthe extract was washed with water
  6. dry with materialan aqueous solution saturated with sodium chloride then was dried with anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue thus obtained
  9. customwas crystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-7916107cf1224db786c3f080c25935af
Source dataset
uspto-grants-1999_12
Patent number
US05998437

Reaction notes

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