Hydrochloric Acid → HCID 66776473, compound

HRID 1618822Notes

Reaction equation

HRID 1618822 reaction equation
[Mg].BrCCBr.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[N:14]=2)=[CH:9][CH:8]=1.[Br:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1.Cl>O1CCCC1>[Br:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:17]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:16]4[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=4[N:14]=3)=[CH:9][CH:8]=2)=[O:34])=[CH:31][CH:30]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 685154-Bromobenzoyl chlorideHCID 5462224MagnesiumHCID 230940702-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazole

Product 1

HCID 66776473HCID 66776473, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In a 300 mL three-neck flask, 410 mg (17 mmol) of active magnesium was stirred in 5 mL of dehydrated tetrahydrofuran (THF), and about 0.2 mL of 1,2-dibromoethane was added thereto, so that bubble release and heat generation were confirmed. A solution in which 5.2 g (15 mmol) of 4-bromophenyl-1-phenyl-1H-benzimidazole has been dissolved in 50 mL of dehydrated THF was added thereto. The mixture was heated and stirred for 4 hours, and then cooled to room temperature, so that a Grignard reagent was prepared. Then, in a 500 mL three-neck flask were put 3.7 g (17 mmol) of 4-bromobenzoyl chloride and 150 mL of dehydrated THF, and the mixture was stirred at −40° C. The above Grignard reagent was dropped into the mixture, the mixture was stirred for 1 hour, and then stirred at room temperature for about 15 hours. After reaction, 1N-hydrochloric acid was added to the mixture until the mixed solution became acid. An organic phase of the obtained mixed solution was washed with water, and then magnesium sulfate was added thereto so that moisture was adsorbed. This suspension was filtered, the resulting filtrate was concentrated, and ethyl acetate and toluene were added to perform recrystallization. As a result, 2.5 g of powder was obtained. The reaction scheme is shown in (A-1).

Workup

  1. customso that bubble release
  2. temperatureheat generation
  3. additionwas added
  4. temperatureThe mixture was heated
  5. customwas prepared
  6. customThen, in a 500 mL three-neck flask were put
  7. stirringthe mixture was stirred for 1 hour
  8. stirringstirred at room temperature for about 15 hours
  9. additionwas added to the mixture until the mixed solution
  10. additionAn organic phase of the obtained mixed solution
  11. washwas washed with water
  12. additionmagnesium sulfate was added
  13. filtrationThis suspension was filtered
  14. concentrationthe resulting filtrate was concentrated
  15. additionethyl acetate and toluene were added
  16. customrecrystallization

Sources & evidence

ORD record
ord-889417456f1f469f82ecb56fe8207681
Source dataset
uspto-grants-2014_07
Patent number
US08771843B2

Reaction notes

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