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Sodium Hydroxide → HCID 178441450, compound

HRID 488008
Notes
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Reaction equation

HRID 488008 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=3[C:24]#[N:25])=[CH:13][CH:12]=2)[C:8]2[CH:26]=[CH:27][CH:28]=[CH:29][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[N-:30]=[N+:31]=[N-:32].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C)C=O.C(O)(=O)C.C(OCC)(=O)C>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=3[C:24]3[NH:32][N:31]=[N:30][N:25]=3)=[CH:15][CH:16]=2)[C:8]2[CH:26]=[CH:27][CH:28]=[CH:29][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 224180032-n-Butyl-1-{(5'-chloro-2'-cyanobiphenyl-4-yl)methyl]benzimidazole

Product 1

HCID 178441450HCID 178441450, compound

Reagents, catalysts & solvents 3

HCID 176
Acetic Acid
Solvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

1.2 g of 2-n-butyl-1-{(5'-chloro-2'-cyanobiphenyl-4-yl)methyl}benzimidazole prepared in Preparation Example 8, 910 mg of sodium azide and 750 mg of ammonium chloride were heated while stirring in 50 ml of dimethylformamide as a reaction solvent at an internal temperature of 125° C. for 50 hr. After cooling, a dilute sodium hydroxide solution and ethyl acetate were added thereto for phase separation, thereby obtaining a watery phase. The watery phase was wealky acidified with acetic acid, extracted with chloroform and washed with water. The extract was dried over anhydrous magnesium sulfate, and the residue was subjected to silica gel chromatography (chloroform:etanol:acetic acid=98:2:0.2). A fraction of the intended title compound was concentrated and then recrystallized from ethyl acetate-isopropyl ethermethanol. The yield was 450 mg.

Workup

  1. temperaturewere heated
  2. temperatureAfter cooling
  3. customfor phase separation
  4. customobtaining a watery phase
  5. extractionextracted with chloroform
  6. washwashed with water
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. concentrationA fraction of the intended title compound was concentrated
  9. customrecrystallized from ethyl acetate-isopropyl ethermethanol

Sources & evidence

ORD record
ord-f80e9e377cea4632ae812343ec66b4b4
Source dataset
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05298518

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes