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4-formyl-N,N-bis[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]benzamide → 4-formyl-N,N-bis(1H-imidazol-2-ylmethyl)benzamide

HRID 68649
Notes
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Reaction equation

HRID 68649 reaction equation
[CH:1]([C:3]1[CH:39]=[CH:38][C:6]([C:7]([N:9]([CH2:24][C:25]2[N:26](COCC[Si](C)(C)C)[CH:27]=[CH:28][N:29]=2)[CH2:10][C:11]2[N:12](COCC[Si](C)(C)C)[CH:13]=[CH:14][N:15]=2)=[O:8])=[CH:5][CH:4]=1)=[O:2]>FC(F)(F)C(O)=O.ClCCl>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]([CH2:24][C:25]2[NH:26][CH:27]=[CH:28][N:29]=2)[CH2:10][C:11]2[NH:15][CH:14]=[CH:13][N:12]=2)=[O:8])=[CH:38][CH:39]=1)=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 866542934-formyl-N,N-bis[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]benzamide

Product 1

HCID 862254924-formyl-N,N-bis(1H-imidazol-2-ylmethyl)benzamideYield 99.9%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

To the compound 40 (1.7 g), a 50% trifluoroacetic acid-dichloromethane solution (10 mL) was added. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated and an aqueous 5N sodium hydroxide solution (15 mL) was added to the residue. The aqueous layer was extracted three times with 50 mL of dichloromethane. The combined organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was concentrated to obtain the title compound (compound B) (922 mg) having the following physical properties.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionan aqueous 5N sodium hydroxide solution (15 mL) was added to the residue
  3. extractionThe aqueous layer was extracted three times with 50 mL of dichloromethane
  4. washThe combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-a30393c4b638466c88b7e494e395eefb
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822459B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes