Acetyl chloride → 1H-Benzimidazole-2-methanamine, 6,7-difluoro-, hydrochloride (1:2)

HRID 908245Notes

Reaction equation

HRID 908245 reaction equation
[F:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][NH:12]C(=O)OC(C)(C)C)[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[F:20].C([Cl:24])(=O)C>CO>[ClH:24].[ClH:24].[F:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][NH2:12])[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[F:20]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 58024781HCID 58024781, compound

Product 1

HCID 670578571H-Benzimidazole-2-methanamine, 6,7-difluoro-, hydrochloride (1:2)Yield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a MeOH 144 mL solution of the product obtained in Step B (13.9 g, 48.9 mmol) was added acetyl chloride (16.6 g, 212 mmol) at room temperature. The reaction mixture (solution) was heated to 55° C. in an oil bath for 1 hr and then cooled to room temperature. Resulting suspension was cooled in an ice-water bath and the precipitate was collected by suction filtration and dried to give the title compound (12.5 g). LC/MS; m/z 184(M+H).

Workup

  1. temperaturecooled to room temperature
  2. customResulting suspension
  3. temperaturewas cooled in an ice-water bath
  4. filtrationthe precipitate was collected by suction filtration
  5. customdried

Sources & evidence

ORD record
ord-785d6a04fc594604930832d606d7478a
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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