Trityl chloride → N-Phenyl-1-trityl-1H-imidazol-2-amine

HRID 63227Notes

Reaction equation

HRID 63227 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.[C:21]1([NH:27][C:28]2[NH:29][CH:30]=[CH:31][N:32]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>C(Cl)Cl>[C:21]1([NH:27][C:28]2[N:32]([C:1]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:31]=[CH:30][N:29]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 13805404N-phenyl-1H-imidazol-2-amine

Product 1

HCID 66794278N-Phenyl-1-trityl-1H-imidazol-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trityl chloride (2.79 g, 10 mmol) was added to an ice-cooled solution of phenyl amino imidazole (c) (1.59 g, 10 mmol) and triethylamine (1.01 g, 10 mmol) in methylene dichloride (50 mL). The reaction mixture was allowed to warm to RT and stirred overnight. The mixture was diluted with methylene dichloride, washed successively with H2O, saturated NaHCO3, brine and dried with MgSO4. Filtration and evaporation of the solvent followed by chromatography separation gave the product (d). 1H NMR (500 MHz, CDCl3) δ 7.52-7.35 (m, 5H), 7.28-7.43 (m, 15H), 6.85 (s, 2H), 6.41 (s, 1H), 6.08 (s, 1H). MS: 1399.8 (M−H)−; 402.8 (M+H)+.

Workup

  1. washwashed successively with H2O, saturated NaHCO3, brine
  2. dry with materialdried with MgSO4
  3. filtrationFiltration and evaporation of the solvent
  4. customfollowed by chromatography separation

Sources & evidence

ORD record
ord-e974f0a649e8443db886da1989bc336c
Source dataset
uspto-grants-2016_09
Patent number
US09447049B2

Reaction notes

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