Chloroacetic Acid → 5-chloro-2-(chloromethyl)-1H-1,3-benzodiazole

HRID 1402831Notes

Reaction equation

HRID 1402831 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[Cl:10][CH2:11][C:12](O)=O>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:12]([CH2:11][Cl:10])[NH:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 300Chloroacetic AcidHCID 72634-Chloro-1,2-diaminobenzene

Product 1

HCID 2712865-chloro-2-(chloromethyl)-1H-1,3-benzodiazoleYield 69.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The solution of 4-chloro-1,2-phenylenediamine (1.43 g) and chloroacetic acid (1.43 g) in 4M HCl (10 ml) was heated to reflux for 1 h. After cooling to rt overnight the mixture was filtered and the filtrate was cooled in an ice bath. With stirring the solution was adjusted to pH 8 with 25% ammonia solution. A gummy precipitate is formed which is cooled for 1 h. The aqueous layer is removed by decantation and the residue crystallised from acetone/water to yield 5-chloro-2-chloromethylbenzimidazole (1.4 g) as brownish solid.

Workup

  1. temperatureto reflux for 1 h
  2. filtrationwas filtered
  3. temperaturethe filtrate was cooled in an ice bath
  4. customA gummy precipitate is formed which
  5. temperatureis cooled for 1 h
  6. customThe aqueous layer is removed by decantation
  7. customthe residue crystallised from acetone/water

Sources & evidence

ORD record
ord-fb14993c22a241f48bb602afa6032bab
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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