Hydrochloric Acid → 1H-Benzimidazole, 2-heptadecyl-

HRID 847242Notes

Reaction equation

HRID 847242 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9](O)(=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].Cl.[OH-].[Na+]>O>[CH2:25]([C:26]1[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=1)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5281Stearic AcidHCID 7243O-PhenylenediamineHCID 14798Sodium Hydroxide

Product 1

HCID 798681H-Benzimidazole, 2-heptadecyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

Into a four-necked flask of 2 l capacity were charged 54.0 g (0.5 mol) of o-phenylenediamine, 142 g (0.5 mol) of stearic acid and 500 ml of 4N-hydrochloric acid, and a reaction was effected for 5 hours while refluxing the reaction solution. Then, 500 ml of water was added to the reaction mass, and the resulting solution was neutralized up to a pH of 9.2 at a temperature of not higher than 15° C. with a 20% aqueous solution of sodium hydroxide. Then, the resulting mixture was stirred at a temperature of not higher than 15° C. for 1 hour, and then filtered. The filter cake was washed with water to obtain the aimed 2-heptadecylbenzimidazole in an yield of 139.5 g (78.4%).

Workup

  1. temperaturewhile refluxing the reaction solution
  2. customhigher than 15° C.
  3. filtrationfiltered
  4. washThe filter cake was washed with water

Sources & evidence

ORD record
ord-ba47ca88843d470eb3599fbebdbed0a6
Source dataset
uspto-grants-1992_08
Patent number
US05140055

Reaction notes

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