Sodium Hydroxide → HCID 21875586, compound

HRID 50435Notes

Reaction equation

HRID 50435 reaction equation
CO[C:3]1[CH:35]=[CH:34][C:6]2[NH:7][CH:8]([CH2:32][CH3:33])[N:9]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][C:19]([NH:21][S:22]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=4)(=[O:24])=[O:23])=[O:20])=[CH:12][CH:11]=3)[C:5]=2[CH:4]=1.[OH-:36].[Na+]>Br>[CH2:32]([C:8]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][C:19]([NH:21][S:22]([C:25]3[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=3)(=[O:24])=[O:23])=[O:20])=[CH:12][CH:11]=2)[C:5]2[CH:4]=[CH:3][C:35]([OH:36])=[CH:34][C:6]=2[N:7]=1)[CH3:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 218757625-Methoxy-2-ethyl-3-(4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)amino]ethyl}phenyl)-1H-benzimidazole

Product 1

HCID 21875586HCID 21875586, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

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-91e3bad74386410bb9e6836fb30362c0
Source dataset
uspto-grants-2004_03
Patent number
US06710054B2

Reaction notes

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