Trityl chloride → 4-Methyl-1-trityl-1H-imidazole

HRID 1929556Notes

Reaction equation

HRID 1929556 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.C(N(CC)CC)C.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>CN(C)C=O>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([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:6]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178418800HCID 178418800, compound

Product 1

HCID 6182544-Methyl-1-trityl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 equivalent (i.e. 36.53 mmol, 1 eq.) of 4-methyl-1H-imidazole (1) was dissolved in 120 mL of dimethylformamide, triethylamine (73.06 mmol, 2 eq.) and chlorotriphenylmethane (40.1 mmol, 1.1 eq) where added. The mixture was stirred for 3.5 h. The precipitate filtered off and was washed by means of ice-cooled dimethylformamide (2×50 mL) and water (2×50 mL). After removal of the solvent the remaining product was dried over P4O10.

Workup

  1. filtrationThe precipitate filtered off
  2. washwas washed by means of ice-
  3. temperaturecooled dimethylformamide (2×50 mL) and water (2×50 mL)
  4. customAfter removal of the solvent the remaining product
  5. dry with materialwas dried over P4O10

Sources & evidence

ORD record
ord-1ad4c4e94bdc4354809420dea69c72eb
Source dataset
uspto-grants-2012_05
Patent number
US08188094B2

Reaction notes

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