HCID 14322382, compound → HCID 11613186, compound

HRID 1693500Notes

Reaction equation

HRID 1693500 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9](Cl)[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[CH:4][CH:3]=1.C([O:21][C:22]([C:24]1[N:25]=[CH:26][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:28]=1[NH2:29])=O)C>ClCCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:22](=[O:21])[C:24]3[N:25]=[CH:26][N:27]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:28]=3[N:29]=[C:9]2[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14322382HCID 14322382, compoundHCID 57897867HCID 57897867, compound

Product 1

HCID 11613186HCID 11613186, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of N-(4-bromo-phenyl)-2,4-dichloro-benzimidoyl chloride (0.22 mmol) and 5-amino-1-phenyl-1H-imidazole-4-carboxylic acid ethyl ester (65 mg, 0.27 mmol) in 1,2-dichloroethane is added titanium tetrachloride (98 μL, 0.89 mmol) dropwise at room temperature. After addition is completed, the reaction mixture is heated at 120° C. for 18 hours. After the reaction is quenched with water and the aqueous layer is extracted with ethyl acetate. The organic solvents are combined and dried over magnesium sulfate. Filtration and concentration provide a crude product which is purified by column chromatography gave a white solid as product (41 mg, three steps yield 36%). 1H NMR (CDCl3) δ(ppm) 8.04 (s, 1H), 7.58 (d, 2H), 7.47 (t, 2H), 7.38 (m, 3H), 7.22 (d, 1H), 7.15 (b, 1H), 7.07 (m, 2H), 6.91 (b, 1H); HPLC-MS calculated for C23H13BrCl2N40 (M+H+): 511.0. Found: 511.0.

Workup

  1. additionAfter addition
  2. customAfter the reaction is quenched with water
  3. extractionthe aqueous layer is extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-7dc0a17cce1243049e840ae6b723c487
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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