Sodium Hydroxide → 2H-Benzimidazol-2-one, 1,3-dihydro-6-chloro-1-(4-chlorophenyl)-

HRID 1680686Notes

Reaction equation

HRID 1680686 reaction equation
[OH-].[Na+].[CH:3]1[C:8]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[O:11])=[CH:7][CH:6]=[C:5]([Cl:20])[CH:4]=1.Cl[O-].[Na+]>O.CO>[Cl:20][C:5]1[CH:4]=[CH:3][C:8]2[NH:9][C:10](=[O:11])[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[C:7]=2[CH:6]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 949964,4'-DichlorocarbanilideHCID 23665760Sodium Hypochlorite

Product 1

HCID 2094872H-Benzimidazol-2-one, 1,3-dihydro-6-chloro-1-(4-chlorophenyl)-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (4 grams (g)) in water (15 milliliters (ml)) was added to a solution of 4,4'-dichlorocarbanilide (14.1 g, 0.05 mole) in methanol (300 ml). Sodium hypochlorite solution (100 ml, 1 N in 0.1 molar sodium hydroxide) was then added dropwise over 30 minutes to the vigorously stirred reaction mixture, maintaining the temperature below 35° C. by means of an ice bath. Stirring was continued at room temperature for 5 hours after which the small amount of solid present was removed by filtration. The filtrate was evaporated to a volume of about 50 ml, diluted with water (500 ml), and subsequently acidified to a pH of 3 with hydrochloric acid. The product was then filtered, washed with water, dried at 80° C. and identified as 6-chloro-1-(4-chlorophenyl)-2-benzimidazolinone by infrared spectra. The product recovery was 66 percent of theoretical and the product melted at 239° C. (recrystallized from toluene).

Workup

  1. temperaturemaintaining the temperature below 35° C. by means of an ice bath
  2. customafter which the small amount of solid present was removed by filtration
  3. customThe filtrate was evaporated to a volume of about 50 ml
  4. additiondiluted with water (500 ml)
  5. filtrationThe product was then filtered
  6. washwashed with water
  7. customdried at 80° C.

Sources & evidence

ORD record
ord-52c9477683c04374810447eef3a0c095
Source dataset
uspto-grants-1981_06
Patent number
US04275215

Reaction notes

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