Trityl chloride → 2-Methyl-1-tritylimidazole

HRID 423097Notes

Reaction equation

HRID 423097 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.Cl[C:15]([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:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCCC(C)C>C(#N)C.O>[CH3:8][C:9]1[N:10]([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:11]=[CH:12][N:13]=1

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 78922-MethylpentaneHCID 8471TriethylamineHCID 127492-Methylimidazole

Product 1

HCID 6182462-Methyl-1-tritylimidazoleYield 97.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Triethylamine (11.54 mL, 82.82 mmol) was added dropwise to 2-methyl-1H-imidazole (4.0 g, 48.72 mmol) and chlorotriphenylmethane (14.94 g, 53.59 mmol) in acetonitrile (120 mL) at room temperature over a period of 20 minutes under nitrogen. The resulting suspension was stirred at room temperature for 18 hours. Water (120 mL) and i-hexane (12 mL) were added and the slurry stirred for 30 minutes before filtering. The filtered solid was washed with water (3×15 mL) and dried under vacuum to afford 2-methyl-1-trityl-1H-imidazole (15.41 g, 97%) as a cream solid which was used without further purification.

Workup

  1. stirringthe slurry stirred for 30 minutes
  2. filtrationbefore filtering
  3. washThe filtered solid was washed with water (3×15 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-ab90862bf336477eadde5a44876bc0ac
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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