Hydrochloric Acid → HCID 22288832, compound

HRID 2119581Notes

Reaction equation

HRID 2119581 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-9f63285fa6ba452f84ea780a62f4a3f6
Source dataset
uspto-grants-2004_02
Patent number
US06686384B2

Reaction notes

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