Dichloromethane → HCID 67254310, compound

HRID 2068272Notes

Reaction equation

HRID 2068272 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH2:10].[OH-].[K+].Br[CH2:14][CH2:15][CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(Cl)Cl>CC(C)=O>[Si:18]([O:17][CH2:16][CH2:15][CH2:14][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH2:10])([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 136242-AminobenzimidazoleHCID 14797Potassium HydroxideHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilane

Product 1

HCID 67254310HCID 67254310, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1H-Benzoimidazol-2-ylamine (1 g, 7.5 mmol) was dissolved in acetone (30 mL) and powdered potassium hydroxide (2.12 g, 37.5 mmol) was added. The reaction was allowed to stir for several minutes at room temperature before (3-bromopropoxy)(tert-butyl)dimethylsilane (1.75 mL, 7.5 mmol) was added. After 1 hour, methylene chloride was added and the mixture was washed with water, brine and dried over magnesium sulfate. Upon concentration the crude product was dissolved in methylene chloride and purified by combiflash chromatography, methylene chloride to methylene chloride 6% MeOH gradient, to give 1-(3-(tert-butyldimethylsilyloxy)propyl)-1H-benzo[d]imidazol-2-amine (0.400 g, 1.3 mmol).

Workup

  1. additionwas added
  2. washthe mixture was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationUpon concentration the crude product
  5. dissolutionwas dissolved in methylene chloride
  6. custompurified by combiflash chromatography, methylene chloride to methylene chloride 6% MeOH gradient

Sources & evidence

ORD record
ord-80e1d41f17fb4a479f33dcd21b96a7fb
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

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