Hydrochloric Acid → HCID 22288836, compound

HRID 2119571Notes

Reaction equation

HRID 2119571 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].Cl[C:11]1[NH:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1.Cl>C(O)C>[ClH:1].[NH:12]1[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=[C:11]1[NH:4][C:3]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68972-Chloro-6-methylanilineHCID 785722-Chlorobenzimidazole

Product 1

HCID 22288836HCID 22288836, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-6-methylaniline (0.46 g) and 2-chlorobenzimidazole (0.5 g) were mixed in a flask and then kept at 170° C. for 30 min. After cooling, the residue was dissolved out of the flask with 1 N HCl and 10% ethanol at boiling heat. The material dissolved out was then stirred at RT for 30 min, then the insoluble material was filtered off with suction and the filtrate was evaporated. The residue was purified by means of preparative HPLC on RP-18 using acetonitrile/water (0.05% TFA). The clean fractions were combined, the acetonitrile was stripped off, the residue was adjusted to pH 10 with potassium carbonate solution, extracted three times with EA, and then the combined phases were dried, filtered, and concentrated. The residue was taken up using HCl/water and freeze-dried. 227 mg of the title compound were obtained.

Workup

  1. temperatureAfter cooling
  2. temperatureat boiling heat
  3. dissolutionThe material dissolved out
  4. filtrationthe insoluble material was filtered off with suction
  5. customthe filtrate was evaporated
  6. customThe residue was purified by means of preparative HPLC on RP-18 using acetonitrile/water (0.05% TFA)
  7. extractionextracted three times with EA
  8. customthe combined phases were dried
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customfreeze-dried

Sources & evidence

ORD record
ord-7f49022555624429a4fe83f1ea853e49
Source dataset
uspto-grants-2004_02
Patent number
US06686384B2

Reaction notes

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