Potassium Carbonate → 3-Amino-2-(1-[3,4-dimethylphenylcarbonylmethyl]benzimidazol-2-yl)-1,2,4-triazole

HRID 553019

Reaction equation

HRID 553019 reaction equation
[NH2:1][C:2]1[N:3]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[N:4]=[CH:5][N:6]=1.[CH3:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=1[CH3:27])[C:20](=[O:23])[CH2:21]Br.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:1][C:2]1[N:3]([C:7]2[N:11]([CH2:21][C:20]([C:19]3[CH:24]=[CH:25][C:26]([CH3:27])=[C:17]([CH3:16])[CH:18]=3)=[O:23])[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[N:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6082642-(1H-Benzoimidazol-2-YL)-2H-[1,2,4]triazol-3-ylamineHCID 37031132-Bromo-1-(3,4-dimethylphenyl)ethan-1-one

Product 1

HCID 112332783-Amino-2-(1-[3,4-dimethylphenylcarbonylmethyl]benzimidazol-2-yl)-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 3-amino-2-(1H-benzimidazol-2-yl)-1,2,4-triazole (0.15 g, 0.75 mol), 3,4-dimethyl phenacyl bromide (0.204 g, 0.9 mmol) and dry potassium carbonate (0.258 g, 1.87 mmol) is stirred at room temperature for 16 hours. The mixture is diluted with water and the product extracted with ethyl acetate. The product is purified by chromatography on silicagel. M.p. 190-193° C., 1H-NMR (400 MHz, d6-DMSO): 7.84 (m, 1H); 7.77 (m, 3H); 7.65 (m, 2H); 7.50 (s, 1H); 7.33 (d, 1H); 6.22 (s, 2H); 2.30 (s, 6H).

Workup

  1. extractionthe product extracted with ethyl acetate
  2. customThe product is purified by chromatography on silicagel

Sources & evidence

ORD record
ord-779d95b0aff54cba9a4dcb97837b3204
Source dataset
uspto-grants-2011_05
Patent number
US07951957B2

Linked notes

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