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

HRID 1946473Notes

Reaction equation

[CH3:1][CH:2]([C:4]1[NH:8][C:7]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:14])[C:6]=2[N:5]=1)[CH3:3].[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:19]Br.C1(C)C=CC=CC=1.[NH4+].[Cl-]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[Cl:15][C:16]1[CH:17]=[C:18]([CH2:19][N:5]2[C:6]3[C:13](=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][C:7]=3[N:8]=[C:4]2[CH:2]([CH3:1])[CH3:3])[CH:21]=[CH:22][C:23]=1[Cl:24]

Participants

Conditions

Temperature: 30 °C

Procedure

Tetrabutylammonium bromide (419 mg) was added to a stirred mixture of Intermediate 2 (500 mg, 2.60 mmol) and 3,4-dichlorobenzylbromide (624 mg) in sodium hydroxide 20% aq (3.50 mL) and Toluene (9 mL). The RM was stirred at 30° C. 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 the title compound (630 mg). LC/MS MH+ 351/353, Rt 3.16 min (5 minute run).

Workup

extractionthe mixture was extracted with EtOAc (3×30 ml)
customdried (hydrophobic frit)
concentrationconcentrated under vacuum
customThe residue was purified on silica using a cyclohexane
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-b7c1e09444e4404a83f694d118453e91
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399444B2

Reaction notes

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