Hydrogen Bromide → HCID 21876086, compound

HRID 2077704Notes

Reaction equation

HRID 2077704 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]3[CH:15]=[CH:16][C:17]([O:19]C)=[CH:18][C:13]=3[N:12]=[C:11]2[CH2:21][CH3:22])=[CH:6][CH:5]=1.[OH-].[Na+].[BrH:25]>>[Br:25][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]3[CH:15]=[CH:16][C:17]([OH:19])=[CH:18][C:13]=3[N:12]=[C:11]2[CH2:21][CH3:22])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 21876391HCID 21876391, compound

Product 1

HCID 21876086HCID 21876086, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 1-[4-(2-chloroethyl)phenyl]-2-ethyl-5-methoxy-1H-benzimidazole (step 5 of Example 71, 600 mg, 1.9 mmol) in 48% hydrobromic acid (60 mL) was stirred at 100° C. for 6 h. After cooling, the mixture was neutralized with 2N aqueous NaOH and extracted with ethyl acetate (100 mL). The organic layer was washed with brine (50 mL), dried (Na2SO4), and concentrated to afford 890 mg (quant.) of the title compound as pale yellow solids: 1H-NMR (CDCl3) δ 7.64 (4H, s), 7.16 (2H, m), 6.97-7.01 (1H, m), 3.86 (2H, t, J=7.1 Hz), 3.30 (2H, t, J=7.1 Hz), 2.92 (2H, q, J=7.8 Hz), 1.29 (3H, t, J=7.8 Hz).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-89a319b882844201a421309fcf9ab80e
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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