Hydrogen Peroxide → HCID 68130391, compound

HRID 1581145Notes

Reaction equation

HRID 1581145 reaction equation
[ClH:1].[ClH:2].[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]=1[NH:12][C:13]1[NH:14][CH2:15][CH2:16]N=1.OO>Cl>[ClH:1].[Cl:1][C:9]1[C:10]([Cl:2])=[CH:11][C:6]2[N:5]=[C:4]([N:12]3[CH2:16][CH2:15][N:14]=[CH:13]3)[NH:3][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 191073Brl 8242

Product 1

HCID 68130391HCID 68130391, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

2-(Benzimidazolyl)amino-2-imidazoline dihydrochloride (prepared as described in Example 14) (27.4 g, 0.10 mol) was dissolved in concentrated hydrochloric acid (300 ml). The solution was stirred and heated to 80°C. A 15% solution of hydrogen peroxide (68 ml) was added dropwise to the stirred solution maintaining the temperature at 80°C. A colourless crystalline precipitate was soon deposited. At the end of the addition the solution was filtered, whilst hot and the precipitate washed with water and dried. This first crop (22.8 g), m.p. 275°-285°C, was found to be a mixture of chlorinated products. The second crop of crystals was deposited from the filtrate on cooling and was collected, washed with water and dried. This second crop (4.26g), m.p. 278°-281°C was found to be substantially pure 5,6-dichlorinated product. The first crop was recrystallised from aqueous dimethylformamide. The first (2.28 g), m.p. 297°-298°C, and second (6.42 g) m.p. 282°C crops of this recrystallisation were discarded, but the third crop (11.60 g) m.p. 252°-262°C was found to mainly 5,6-dichlorinated material. Both crops of 5,6-dichlorinated product were combined and recrystallised from boiling water to give 2-(5,6-dichlorobenzimidazolyl-2-imidazoline monohydrochloride (9.83 g; 29%) as colourless microcrystals m.p. 279°-281°C.

Workup

  1. temperaturemaintaining the temperature at 80°C
  2. additionAt the end of the addition the solution
  3. filtrationwas filtered
  4. washwhilst hot and the precipitate washed with water
  5. customdried
  6. additiona mixture of chlorinated products
  7. temperatureon cooling
  8. customwas collected
  9. washwashed with water
  10. customdried
  11. customThe first crop was recrystallised from aqueous dimethylformamide
  12. customThe first (2.28 g), m.p. 297°-298°C, and second (6.42 g) m.p. 282°C crops of this recrystallisation
  13. customrecrystallised

Sources & evidence

ORD record
ord-b64ad26be6d64129839022faa5485d3f
Source dataset
uspto-grants-1976_01
Patent number
US03935314

Reaction notes

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