Chloroacetic Acid → 7-chloro-2-(chloromethyl)-1-methyl-1H-benzo[d]imidazole

HRID 1189250Notes

Reaction equation

HRID 1189250 reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:10])[C:7]=1[NH:8][CH3:9].[Cl:11][CH2:12][C:13](O)=O.[OH-].[Na+].[ClH:18]>>[Cl:18][C:2]1[C:7]2[N:8]([CH3:9])[C:13]([CH2:12][Cl:11])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 126932366-Chloro-N1-methylbenzene-1,2-diamine

Product 1

HCID 436599277-chloro-2-(chloromethyl)-1-methyl-1H-benzo[d]imidazoleYield 40%

Conditions

Temperature
90 °C

Procedure

6-Chloro-N1-methylbenzene-1,2-diamine (800 mg, 5 mmol) and 2-chloroacetic acid (700 mg, 8 mmol) were dissolved in HCl 2N (5.7 mL). The resulting solution was heated at 90° C. for 18 h. The aqueous layer was neutralized by 3N NaOH. After extraction with EtOAc (3*10 mL), the organic layer was washed with water (10 mL), brine (10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the resulting crude product was purified over silicagel chromatography (prepacked 25 g silicagel column, Cyclohexane/AcOEt:70/30 as eluent) to afford 478 mg of 7-chloro-2-(chloromethyl)-1-methyl-1H-benzo[d]imidazole (Yield: 40%) as a pink solid

Workup

  1. extractionAfter extraction with EtOAc (3*10 mL)
  2. washthe organic layer was washed with water (10 mL), brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe resulting crude product was purified over silicagel chromatography (prepacked 25 g silicagel column, Cyclohexane/AcOEt:70/30 as eluent)

Sources & evidence

ORD record
ord-123326955312483b973374ffc2fbb468
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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