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Ammonium Chloride → HCID 178420302, compound

HRID 456823
Notes
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Reaction equation

HRID 456823 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=[C:9]1[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([O:29][CH2:30][C:31]#[N:32])[CH:23]=[CH:22]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].[N-:35]=[N+:36]=[N-:37].[Na+]>CN(C=O)C.C(Cl)Cl>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][CH:10]=[C:9]1[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([O:29][CH2:30][C:31]1[NH:37][N:36]=[N:35][N:32]=1)[CH:23]=[CH:22]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18439031{[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetonitrile

Product 1

HCID 178420302HCID 178420302, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

In a similar manner as described in step 2 of Example 3, the title compound was prepared from {[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetonitrile (0.20 g, 48 mmol), prepared in the previous step, ammonium chloride (0.077 g, 1.44 mmol) and sodium azide (0.094 g, 1.44 mmol) in DMF (10 mL). The solids were isolated by vacuum filtration and dissolved in methylene chloride. The organic solution was dried (MgSO4), filtered and the solvent removed under reduced pressure to give 5-({[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}methyl)-1H -tetraazole as an amorphous beige solid (0.203 g, 92%), mp 190–200° C. (dec). Elemental Analysis for C29H23N5O.0.49 H2O.0.21 C3H7NO Calc'd: C, 73.90; H, 5.32; N, 15.15. Found: C, 73.05, H, 5.25; N, 15.03.

Workup

  1. customThe solids were isolated by vacuum filtration
  2. dry with materialThe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ab60603cd7154bc6809055954f51e67e
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07186749B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes