Trityl chloride → 4-(2-bromophenyl)-1-trityl-1H-imidazole

HRID 1795256Notes

Reaction equation

HRID 1795256 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[CH:10][NH:11][CH:12]=1.C(N(CC)CC)C.[C:20](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[CH:10][N:11]([C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178419371HCID 178419371, compound

Product 1

HCID 221851434-(2-bromophenyl)-1-trityl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of crude 4-(2-bromo-phenyl)-1H-imidazole (73.5 g, 0.33 mol) and triethylamine (45.8 ml, 0.33 mol) in dry dimethylformamide (750 ml) at 0° C. was added a solution of trityl chloride in dry dimethylformamide (850 ml) dropwise over 40 min. When the addition was complete, the ice bath was removed and the reaction was stirred at room temperature for 1.5 h. Then the reaction mixture was poured into a stirring mixture of ice water (ca. 2.0 L). A light orange solid precipitated. After stirring for 20 min the solid was filtered and dried to give a light amber solid. This solid was used in the next reaction without further purification.

Workup

  1. additionWhen the addition
  2. customthe ice bath was removed
  3. additionThen the reaction mixture was poured into a stirring mixture of ice water (ca. 2.0 L)
  4. customA light orange solid precipitated
  5. stirringAfter stirring for 20 min the solid
  6. filtrationwas filtered
  7. customdried
  8. customto give a light amber solid
  9. customThis solid was used in the next reaction without further purification

Sources & evidence

ORD record
ord-e3cf39a8b6f3418d8ab8893de9ee70f4
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

Loading…