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Sodium Iodide → HCID 19600398, compound

HRID 609767
Notes
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Reaction equation

HRID 609767 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]Cl)[CH:25]=[CH:24]2)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:34]1[CH:38]=[N:37][N:36]=[N:35]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(OCC)(=O)C.CCCCCC.O.CN(C)C=O>[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:34]1[CH:38]=[N:37][N:36]=[N:35]1)[CH:25]=[CH:24]2)=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 19600400HCID 19600400, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 19600398HCID 19600398, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent
HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
100 °C

Procedure

To 3.8 g of 1-benzyl-6-chloro-2-[1-(3-chloro-propyl)indol-5-ylaminocarbonyl]benzimidazole was added 100 mg of dimethylformamide, further added 1.4 g of 1H-1,2,3,4-tetrazol, 2.2 g of potassium carbonate and 7.2 g of sodium iodide, the mixture was heated and stirred at 100° C. for 2 days. Water was added to the reaction mixture, and extracted with ethyl acetate, the extract was washed with water and an aqueous solution saturated with sodium chloride. The washed extract was dried with anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1), after separation of isomers, there were obtained 1.1 g of 1-benzyl-6-chloro-2-{1-[3-(1,2,3,4-tetrazol-1-yl)propyl]indol-5-ylaminocarbonyl}benzimidazole (A) as in form of colorless needle crystals by recrystallization from ethyl acetate-n-hexane, and 0.9 g of 1-benzyl-6-chloro-2-{1-[3-(1,2,3,4-tetrazol-2-yl)-propyl]indol-5-ylaminocarbonyl}benzimidazole (B) as in the form of pale yellow needle crystals by recrystallization from dichloromethane-n-hexane.

Workup

  1. temperaturethe mixture was heated
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with water
  4. extractionThe washed extract
  5. dry with materialwas dried with anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe residue thus obtained
  8. customafter separation of isomers

Sources & evidence

ORD record
ord-884992f6c88e4a6eb9d454d34b86fc17
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05998437

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes