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Imidazole sodium → 1-(1H-imidazol-1-yl)-1-[3-[(tert-butoxycarbonyl)amino]phenyl]-methane

HRID 1868216
Notes
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Reaction equation

HRID 1868216 reaction equation
S(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:8]=1)(C)(=O)=O.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.[Na]>CN(C=O)C>[N:21]1([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:8]=2)[CH:25]=[CH:24][N:23]=[CH:22]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 57373095Imidazole sodiumHCID 579821673-[(tert-Butoxycarbonyl)amino]benzyl Methanesulfonate

Product 1

HCID 579821431-(1H-imidazol-1-yl)-1-[3-[(tert-butoxycarbonyl)amino]phenyl]-methaneYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

The title compound from Step A above (14.54 g, 44.8 mmoles) was dissolved in anhydrous DMF (100 mL) and sodium imidazole (6.52 g, 72.4 mmoles) was added. The mixture was heated under argon at 70° C. for 2 h. The solution was evaporated to dryness and chromatographed on silica gel using 2% (10% conc. NH4OH in methanol)-dichloromethane as the eluant to give the title compound (8.92 g, 68%):

Workup

  1. customThe solution was evaporated to dryness
  2. customchromatographed on silica gel using 2% (10% conc. NH4OH in methanol)-dichloromethane as the eluant

Sources & evidence

ORD record
ord-792dbafba8824f77a3bc01c4b51b05cd
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07635697B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes