Trityl chloride → 4-Iodo-1-tritylimidazole

HRID 1584254Notes

Reaction equation

HRID 1584254 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:21][C:22]1[N:23]=[CH:24][NH:25][CH:26]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([N:25]1[CH:26]=[C:22]([I:21])[N:23]=[CH:24]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178506559HCID 178506559, compound

Product 1

HCID 6182524-Iodo-1-tritylimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trityl chloride (3.8 g, 13.6 mmol) was added to a cooled (0° C.) solution of 4-iodoimidazole (2.25 g, 11.6 mmol) and triethylamine (2 ml, 14.3 mmol) in methylene chloride (25 ml). After stirring for 30 min the reaction mixture was warmed to room temperature and stirred ther for 2 h. The reaction mixture was washed well with water and saturated NaHCO3 then dried (Na2SO4). Concentration gave the product as a white solid. 1H NMR (CDCl3) d 6.92 (s, 1 H), 7.08-7.20 (m, 6 H), 7.28-7.40 (m, 10 H).

Workup

  1. stirringstirred ther for 2 h
  2. washThe reaction mixture was washed well with water and saturated NaHCO3
  3. dry with materialthen dried (Na2SO4)
  4. concentrationConcentration

Sources & evidence

ORD record
ord-e364d6705e3042678c5f2a53d7e08633
Source dataset
uspto-grants-1999_08
Patent number
US05932606

Reaction notes

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