Hydrochloric Acid → HCID 22288832, compound

HRID 968303Notes

Reaction equation

HRID 968303 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:9][C:10]1[NH:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1.Cl>>[ClH:9].[NH:11]1[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=[C:10]1[NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7242O-ToluidineHCID 785722-Chlorobenzimidazole

Product 1

HCID 22288832HCID 22288832, compoundYield 9.1%

Procedure

2-Methylaniline (0.5 g) and 2-chlorobenzimidazole (0.71 g) were mixed in a flask and then kept at 250° C. for 2 h. After cooling, the residue was dissolved out of the flask at boiling heat using 1 N HCl, 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 rendered alkaline using potassium carbonate solution, extracted three times with EA, and the combined phases were then dried, filtered, and concentrated. The residue was taken up using 2 N HCl and the solution was freeze-dried. 110 mg of the title compound were obtained.

Workup

  1. temperatureAfter cooling
  2. dissolutionthe residue was dissolved out of the flask
  3. temperatureat boiling heat
  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 then dried
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customthe solution was freeze-dried

Sources & evidence

ORD record
ord-6fb9a6a637be405dbd2a15ad8b070dc8
Source dataset
uspto-grants-2005_10
Patent number
US06958357B2

Reaction notes

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