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Toluene → 3-[(4-chlorophenyl)methyl]-2-(1,1-dimethylethyl)-5,6,7,8-tetrahydrocyclohepta[d]imidazol-4(3H)-one

HRID 1946480
Notes
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Reaction equation

HRID 1946480 reaction equation
[CH3:1][C:2]([C:5]1[NH:9][C:8]2[CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:15])[C:7]=2[N:6]=1)([CH3:4])[CH3:3].[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.C1(C)C=CC=CC=1.[NH4+].[Cl-]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[Cl:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:6]2[C:7]3[C:14](=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][C:8]=3[N:9]=[C:5]2[C:2]([CH3:1])([CH3:3])[CH3:4])=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 584601622-(1,1-dimethylethyl)-5,6,7,8-tetrahydrocyclohepta[d]imidazol-4(1H)-one

Product 1

HCID 584602383-[(4-chlorophenyl)methyl]-2-(1,1-dimethylethyl)-5,6,7,8-tetrahydrocyclohepta[d]imidazol-4(3H)-oneYield 23.8%

Reagents, catalysts & solvents

2
HCID 74236Tetrabutylammonium BromideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

Tetrabutylammonium bromide (1.33 g) was added to a stirred mixture of Intermediate 13 (1.7 g), 4-chlorobenzyl bromide (1.86 g) in sodium hydroxide 20% aq. (12 mL) and toluene (6 mL). The RM was stirred at room temp under nitrogen atm for 3 hours. An excess of sat. NH4Cl aq. solution was added and the mixture was extracted with EtOAc (3×30 ml). The organics were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified on silica using a cyclohexane:ethyl acetate 0-100% gradient. The desired fractions were combined and concentrated under vacuum to give crude material. It was purified by reverse phase chromatography using an acetonitrile-0.1% NH3:water—with an amonium carbonate buffer modifier (pH=10) 5%-95% gradient. The desired fractions were combined and concentrated under vacuum to yield the title compound (650 mg). LC/MS MH+ 331 Rt 2.04 min (5 minute run).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×30 ml)
  2. customdried (hydrophobic frit)
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified on silica using a cyclohexane
  5. concentrationconcentrated under vacuum
  6. customto give crude material
  7. customIt was purified by reverse phase chromatography
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-df2e2cdac8c74228a9505a71cfafeaca
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399444B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes