Boron tribromide → HCID 18789589, compound

HRID 618245Notes

Reaction equation

HRID 618245 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-2b8d6f75577f4ebf94a9d3a58c172859
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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