Trityl chloride → HCID 68674255, compound

HRID 1927651Notes

Reaction equation

HRID 1927651 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[NH:11][CH:12]=[C:13]([CH2:15][C:16]([CH3:20])([CH3:19])[CH2:17][CH3:18])[N:14]=2)=[CH:4][CH:3]=1.[C:21](Cl)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]([C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:12]=[C:13]([CH2:15][C:16]([CH3:19])([CH3:20])[CH2:17][CH3:18])[N:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178442427HCID 178442427, compound

Product 1

HCID 68674255HCID 68674255, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[2-(4-bromophenyl)ethyl]-4-(2,2-dimethylbutyl)-1H-imidazole (33.4 g, 100 mmol) in methlyene chloride (500 mL) was added trityl chloride (41.8 g, 150 mmol) and triethylamine (42 mL, 300 mmol). The reaction was stirred for 2 h, then washed with water, dried over sodium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography eluting with ethyl acetate/hexanes (2:8). The chromatography was repeated eluting with methylene chloride/2-propanol 99.8:0.02) and then methlyene chloride/methanol (95:5) to provide 2-[2-(4-bromophenyl)ethyl]-4-(2,2-dimethylbutyl)-1-trityl-1H-imidazole.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customto give a residue
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with ethyl acetate/hexanes (2:8)
  7. washThe chromatography was repeated eluting with methylene chloride/2-propanol 99.8:0.02) and then methlyene chloride/methanol (95:5)

Sources & evidence

ORD record
ord-5d478cb98f9c4235a309aac6bc0370a1
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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