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

HRID 253473

Reaction equation

HRID 253473 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH2:9].[Cl:10][CH2:11][C:12](O)=O>Cl.O.C(=O)(O)[O-].[Na+]>[Cl:10][CH2:11][C:12]1[N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:9]=1

Participants

6

Reactant 2

HCID 300Chloroacetic AcidHCID 78498N-Methyl-o-phenylenediamine

Product 1

HCID 2480442-(Chloromethyl)-1-methylbenzimidazoleYield 87.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
55 °C

Procedure

N-methyl-phenylenediamine (1 g, 8.2 mmol) and chloroacetic acid (0.9 g, 9.4 mol) were dissolved in 5 N aqueous hydrochloric acid (10 mL) and stirred at 55° C. overnight. The reaction mixture was then diluted with water and basified with solid sodium bicarbonate to give a precipitate which was filtered, washed with water and dried to provide the desired compound (1.3 g, 87%).

Workup

  1. customto give a precipitate which
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ba330bcfa33e419daff6496203bb19c7
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Linked notes

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