Acetyl chloride → 5-Bromo-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole hydrochloride

HRID 74184Notes

Reaction equation

HRID 74184 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[C:6]([CH:8]=1)[NH2:7].[C:16]([Cl:19])(=O)[CH3:17]>C1(C)C=CC=CC=1>[ClH:19].[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([CH:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:16]([CH3:17])=[N:7][C:6]=2[CH:8]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 436098145-Bromo-2-(tetrahydropyran-4-yl)aminoaniline

Product 1

HCID 674980435-Bromo-2-methyl-1-(tetrahydropyran-4-yl)benzimidazole hydrochlorideYield 94.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 2-neck flask was charged with 5-bromo-2-(tetrahydropyran-4-yl)aminoaniline (see Synthesis Example 18-2) (2.72 g, 10.0 mmol) and anhydrous toluene (20 mL) and this was refluxed. To this was added dropwise over approx. 15 m acetyl chloride (1.57 g, 20.0 mmol) in toluene solution (approx. 2.5 mL), and this was stirred under these conditions for 2 hours. After being allowed to cool to room temperature, this was concentrated under reduced pressure and the residue was reslurried in hexane (20 mL). The precipitated crystals were filtered off and washed with hexane. The crystals obtained were dried at reduced pressure with heating to yield the title compound (3.14 g, 94.7% yield) as a light purple solid.

Workup

  1. temperaturethis was refluxed
  2. concentrationthis was concentrated under reduced pressure
  3. filtrationThe precipitated crystals were filtered off
  4. washwashed with hexane
  5. customThe crystals obtained
  6. customwere dried at reduced pressure
  7. temperaturewith heating

Sources & evidence

ORD record
ord-5806728240b34bc394380b0d90037b75
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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