Chloroacetic Acid → Benzimidazole, 2-chloromethyl-5,6-dichloro-

HRID 986664

Reaction equation

HRID 986664 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[Cl:11][CH2:12][C:13](O)=O>Cl>[Cl:11][CH2:12][C:13]1[NH:10][C:4]2[CH:3]=[C:2]([Cl:1])[C:7]([Cl:8])=[CH:6][C:5]=2[N:9]=1

Participants

4

Reactant 2

HCID 300Chloroacetic AcidHCID 792974,5-Dichloro-1,2-phenylenediamine

Product 1

HCID 38349Benzimidazole, 2-chloromethyl-5,6-dichloro-Yield 80.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1.77 g (10 m mol) of 4,5-dichloro-1,2-phenylenediamine in 15 ml of 4N aqueous hydrochloric acid was stored at room temperature overnight. To the solution was added 1.42 g (15 m mol) of monochloroacetic acid, and refluxed for 3 hours and filtered. The filterate was cooled to room temperature, stirred and rendered alkaline by addition of ammonium hydroxide. The separated precipitate was washed with water and dried to give 1.9 g (68%) of the title compound.

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationfiltered
  3. additionby addition of ammonium hydroxide
  4. washThe separated precipitate was washed with water
  5. customdried

Sources & evidence

ORD record
ord-6f3ea686ca0c44848b783cb11ef233c2
Source dataset
uspto-grants-1987_12
Patent number
US04714764

Linked notes

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