Trityl chloride → methyl N-triphenylmethyl-5-benzimidazolecarboxylate

HRID 352843

Reaction equation

HRID 352843 reaction equation
Cl.[N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:10][C:5]=2[NH:4][CH:3]=1.C(N(CC)CC)C.[C:22]1([C:28](Cl)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl>[C:22]1([C:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:2]2[C:6]3[CH:7]=[CH:8][C:9]([C:11]([O:13][CH3:14])=[O:12])=[CH:10][C:5]=3[N:4]=[CH:3]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 22710297methyl 1H-benzimidazole-5-carboxylate hydrochloride

Product 1

HCID 22710354methyl N-triphenylmethyl-5-benzimidazolecarboxylateYield 106.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In dichloromethane (15 ml), methyl 5-benzimidazolecarboxylate hydrochloride (1.00 g) was suspended. To the resulting suspension, triethylamine (1.50 ml) and triphenylmethyl chloride (1.50 g) were added, followed by stirring at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane, washed with water, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (hexane:ethyl acetate=2:1), whereby title compound (2.10 g, quant.) was obtained as a yellow solid.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe residue obtained
  4. distillationby distilling off the solvent under reduced pressure
  5. customwas purified by chromatography on a silica gel column (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-af0bf4a0bddb49e6b50c4a70c60ee1ea
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Linked notes

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