Water → 4-Iodo-1-tritylimidazole

HRID 1826458Notes

Reaction equation

HRID 1826458 reaction equation
[I:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[C:7]1([C:13](Cl)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.O>CN(C)C=O>[I:1][C:2]1[N:3]=[CH:4][N:5]([C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178506559HCID 178506559, compound

Product 1

HCID 6182524-Iodo-1-tritylimidazoleYield 59.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 4-iodo-1H-imidazole (Preparation 71, 3.0 g, 15.3 mmol) in N,N-dimethylformamide (25 ml) was added triphenylmethyl chloride (4.72 g, 16.9 mmol) and then triethylamine (2.5 ml, 18.4 mmol). After stirring at room temperature for 2.5 h, water (200 ml) was added and the reaction mixture was filtered and washed with water. The crude solid was chromatographed on silica gel eluting with hexane:ethyl acetate (5:1 and then 2:1). The material was then recrystallised from hexane and dichloromethane to give the title compound as a white solid (4.0 g, 59%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washwashed with water
  3. customThe crude solid was chromatographed on silica gel eluting with hexane:ethyl acetate (5:1
  4. customThe material was then recrystallised from hexane and dichloromethane

Sources & evidence

ORD record
ord-aa28e8e2b63f4f13978938432f05b9e1
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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