Hydrochloric Acid → N-{2-[4-(5,6-Dichloro-2-ethyl-1H-benzimidazol-1-yl)phenyl]ethyl}hydroxylamine

HRID 858452Notes

Reaction equation

HRID 858452 reaction equation
C(OC([N:8]([O:30]C(OC(C)(C)C)=O)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:21]3[CH:22]=[C:23]([Cl:27])[C:24]([Cl:26])=[CH:25][C:20]=3[N:19]=[C:18]2[CH2:28][CH3:29])=[CH:13][CH:12]=1)=O)(C)(C)C.Cl.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Cl:26][C:24]1[C:23]([Cl:27])=[CH:22][C:21]2[N:17]([C:14]3[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][NH:8][OH:30])=[CH:16][CH:15]=3)[C:18]([CH2:28][CH3:29])=[N:19][C:20]=2[CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 21876184HCID 21876184, compound

Product 1

HCID 21875813N-{2-[4-(5,6-Dichloro-2-ethyl-1H-benzimidazol-1-yl)phenyl]ethyl}hydroxylamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[4-(2-{(tert-butoxycarbonyl)[(tert-butoxycarbonyl)oxy]amino}ethyl)phenyl]-5,6-dichloro-2-ethyl-1H-benzimidazole (step 1, 174 mg, 0.3 mmol) and 2N hydrochloric acid (3 mL) in ethyl acetate (20 mL) was stirred at room temperature for 1 day. The reaction mixture was poured into water (100 mL), neutralized with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate (100 mL). The organic layer was washed with brine (50 mL), dried (Na2SO4), and concentrated to afford 162 mg (quant.) of the title compound as a yellow oil: 1H-NMR (CDCl3) δ 10.35 (2H, br.s), 7.89 (1H, s), 7.46–7.50 (2H, m), 7.29 (2H, d, J=6.8 Hz), 7.17 (1H, s), 3.37 (2H, t, J=6.9 Hz), 3.12 (2H, t, J=6.9 Hz), 2.80 (2H, q, J=6.9 Hz), 1.34 (3H, m).

Workup

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

Sources & evidence

ORD record
ord-944294985f7240e883edb7aa1a974680
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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