Pyridine → 7-bromo-2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole

HRID 923760Notes

Reaction equation

HRID 923760 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([NH2:12])[C:3]=1[NH:13][CH3:14].[CH2:15]([S:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](O)=O)[CH3:16].CCN=C=NCCCN(C)C.N1C=CC=CC=1>O>[Br:1][C:2]1[C:3]2[N:13]([CH3:14])[C:20]([C:19]3[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=3[S:17][CH2:15][CH3:16])=[N:12][C:4]=2[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 4257582-(Ethylsulfanyl)benzoic acidHCID 860613183-bromo-N2-methyl-5-trifluoromethylbenzene-1,2-diamine

Product 1

HCID 679843387-bromo-2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazoleYield 43.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 3-bromo-N2-methyl-5-trifluoromethylbenzene-1,2-diamine (2.22 g), 2-ethylsulfanylbenzoic acid (1.80 g), WSC (1.40 g), and pyridine (10 ml) was stirred under reflux at 115° C. for 6 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.48 g of 7-bromo-2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as Present Compound 74).

Workup

  1. temperatureInto the reaction mixture cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4776a4c3d984da693ad603205c6a3a2
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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