Trityl chloride → 1-(1-trityl-1H-imidazol-4-yl)ethanone

HRID 1398559Notes

Reaction equation

HRID 1398559 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6](=[O:8])[CH3:7])[N:3]=[CH:2]1.C(N(CC)CC)C.[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C.[Cl-].[Na+].O>[C:17]1([C:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:1]2[CH:5]=[C:4]([C:6](=[O:8])[CH3:7])[N:3]=[CH:2]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178467225HCID 178467225, compound

Product 1

HCID 104280901-(1-trityl-1H-imidazol-4-yl)ethanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1-(1H-imidazol-4-yl)ethanone (200 mg, 1.82 mmol) in DMF (4 mL) was introduced triethylamine (0.38 mL, 2.72 mmol) and trityl chloride (506.34 mg, 1.82 mmol). The reaction mixture was stirred at room temperature for 2 h. Aqueous brine solution (5 mL) was added to the reaction mixture and the product extracted with EtOAc (2×10 mL). The combined organics were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography (Isolute, 1-10% methanol gradient in DCM) to give the title intermediate as a clear oil: 1H NMR (500 MHz, CDCl3) delta 2.55 (3H, s), 7.18-7.06 (6H, m), 7.40-7.29 (9H, m), 7.44 (1 H, d, J=1.3 Hz), 7.58 (1H, d, J=1.4 Hz); LC-MS: m/z=+375.10 (M+Na)+.

Workup

  1. extractionthe product extracted with EtOAc (2×10 mL)
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography (Isolute, 1-10% methanol gradient in DCM)

Sources & evidence

ORD record
ord-92d38d9c3aa04433af50b128461af799
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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