Boron tribromide → HCID 18789589, compound

HRID 1106753Notes

Reaction equation

HRID 1106753 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:18]C)=[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:12]=1.B(Br)(Br)[Br:21]>ClCCl>[BrH:21].[NH:3]1[CH2:4][CH2:5][N:1]=[C:2]1[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:18])=[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18789599HCID 18789599, compound

Product 1

HCID 18789589HCID 18789589, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 420 mg of N-[5-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2-methoxy-phenyl]-methanesulfonamide (free base) in 24 ml of dichloromethane was cooled in an ice bath and treated with 10.3 ml of 1M boron tribromide in dichloromethane. Removed the ice bath, stirred at room temperature for 3 hr, added methanol, and evaporated. The residue was purified by flash chromatography on silica gel eluting with dichloromethane/methanol/concentrated ammonium hydroxide (85:5:3) and crystallized from ethanol/ether to afford 58 mg of N-[5-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2-hydroxy-phenyl]-methanesulfonamide hydrobromide, mp 209-209.5° C.

Workup

  1. customRemoved the ice bath
  2. additionadded methanol
  3. customevaporated
  4. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane/methanol/concentrated ammonium hydroxide (85:5:3)
  5. customcrystallized from ethanol/ether

Sources & evidence

ORD record
ord-96a59e4dc3ef4967b9f5edb3d283fe84
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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