Hydrogen Peroxide → HCID 21561685, compound

HRID 1581147Notes

Reaction equation

HRID 1581147 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:17]=1.OO>Cl.O>[Cl:1][C:10]1[C:9]([Cl:2])=[CH:8][C:7]2[N:3]=[C:4]([NH:12][C:13]3[NH:14][CH2:15][CH2:16][N:17]=3)[NH:5][C:6]=2[CH:11]=1

Participants

5

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 191073Brl 8242

Product 1

HCID 21561685HCID 21561685, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

2-(2-Benzimidazolyl) amino-2-imidazoline dihydrochloride (13.7g, 0.05 mol) was dissolved in concentrated hydrochloric acid (100 ml) and water (100 ml). The solution was stirred and heated to 70°C. A 10% solution of hydrogen peroxide (27 ml) was added dropwise over 10 minutes resulting in precipitation of a white solid. Water (100 ml) was added to cool the reaction mixture to 60°C. A further quantity of 10% hydrogen peroxide (10.5 ml; 10% excess in all) was added. The reaction mixture was heated to 80°C for 15 minutes, and filtered whilst hot to give a solid m.p. 265°-272°C. The filtrate was cooled to give more solid m.p. 285°-292°C. Finally evaporation of the mother liquors in vacuo yielded a third quantity. All 3 solids were combined and recrystallised twice from water to yield 2-(5,6-Dichloro-2-benzimidazolyl) amino-2-imidazoline hydrochloride (7.86g; 53%) as colourless microcrystals m.p. 279° -281°C.

Workup

  1. customresulting in precipitation of a white solid
  2. temperatureto cool the reaction mixture to 60°C
  3. addition10% excess in all) was added
  4. temperatureThe reaction mixture was heated to 80°C for 15 minutes
  5. filtrationfiltered whilst hot

Sources & evidence

ORD record
ord-40a60e717b8f4ae2bd0220c00cfb452e
Source dataset
uspto-grants-1976_01
Patent number
US03935314

Reaction notes

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