Trityl chloride → HCID 12076919, compound

HRID 1584251Notes

Reaction equation

HRID 1584251 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:12])/[CH:5]=[CH:6]/[C:7]1[N:8]=[CH:9][NH:10][CH:11]=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>C(Cl)(Cl)Cl>[CH3:2][O:3][C:4](=[O:12])/[CH:5]=[CH:6]/[C:7]1[N:8]=[CH:9][N:10]([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:11]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178500032HCID 178500032, compound

Product 1

HCID 12076919HCID 12076919, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of trans-4-imidazoleacrylic acid methyl ester hydrochloride (20.0 g, 106 mmol) and triethylamine (44 ml, 318 mmol) in chloroform (500 ml) was added a solution of trityl chloride (29.5 g, 318 mmol) in chloroform (100 ml). The resulting suspension was stirred at room temperature for 24 h. The reaction mixture was then washed with water and dried over MgSO4. Filtration and removal of the solvent in vacuo to gave the title compound as a tan solid: 1H NMR (CDCl3) d 3.75 (s, 3 H), 6.54 (d, J=16 Hz, 1 H) 7.03 (s, 1 H), 7.13-7.34 (m, 15 H) 7.46 (s, 1 H), 7.51 (d, J=16 Hz 1 H).

Workup

  1. washThe reaction mixture was then washed with water
  2. dry with materialdried over MgSO4
  3. filtrationFiltration and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-d8a1c1cc7cf14099969e50a11bb73684
Source dataset
uspto-grants-1999_08
Patent number
US05932606

Reaction notes

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