Chloroacetic Acid → 2-(Chloromethyl)-1-methylbenzimidazole

HRID 495255

Reaction equation

HRID 495255 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-])=O.[H][H].[Cl:14][CH2:15][C:16](O)=O.Cl.C(=O)(O)[O-].[Na+]>[Pd].O.C(O)C>[Cl:14][CH2:15][C:16]1[N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:9]=1

Participants

9

Reactant 5

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 69157Benzenamine, N-methyl-2-nitro-HCID 516892Sodium BicarbonateHCID 178418361HCID 178418361, compound

Product 1

HCID 2480442-(Chloromethyl)-1-methylbenzimidazoleYield 77.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a pressure reaction bottle was added 4 g N-methyl-2-nitroaniline, 0.44 g 5% palladium on carbon, and 100 ml ethanol. The mixture was hydrogenated at 22 C and 40 psi hydrogen for 2 hours. Following filtration through celite, and solvent removal, a dark red oil was obtained. To this oil was added 3.7 g chloroacetic acid and 40 ml 5M hydrochloric acid. After refluxing under nitrogen for 2.5 hours, the mixture was cooled to 22 C, diluted with 200 ml water, and neutralized with solid sodium bicarbonate. The resulting solid was filtered, washed with water and dried giving 3.7 g gray solid.

Workup

  1. customTo a pressure reaction bottle
  2. filtrationfiltration
  3. customthrough celite, and solvent removal
  4. customa dark red oil was obtained
  5. temperatureAfter refluxing under nitrogen for 2.5 hours
  6. temperaturethe mixture was cooled to 22 C
  7. filtrationThe resulting solid was filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-85cb25830ff741ebbf8f07b571cd5dc8
Source dataset
uspto-grants-2009_05
Patent number
US07538931B2

Linked notes

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