Ammonium Chloride → HCID 21875779, compound

HRID 1454635Notes

Reaction equation

HRID 1454635 reaction equation
[C:1]([O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([N+:23]([O-])=O)=[CH:22][C:17]=3[N:16]=[C:15]2[CH2:26][CH3:27])=[CH:10][CH:9]=1)(=[O:4])[CH2:2][CH3:3].[Cl-].[NH4+]>C(O)C.O.[Fe]>[C:1]([O:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([NH2:23])=[CH:22][C:17]=3[N:16]=[C:15]2[CH2:26][CH3:27])=[CH:12][CH:13]=1)(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 21876402HCID 21876402, compound

Product 1

HCID 21875779HCID 21875779, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a stirred solution of 2-[4-(2-ethyl-5-nitro-1H-benzimidazol-1-yl)phenyl]ethyl propionate (step 3, 1.12 g, 3.0 mmol) in ethanol/water (v/v, 2:1, 15 mL) was added ammonium chloride (80 mg, 1.5 mmol) and iron powder (840 mg, 15 mmol) at room temperature. The mixture was heated at reflux temperature for 4 h and filtered through a pad of Celite. The filtrate was concentrated, and the residue was dissolved in dichloromethane (200 mL), then dried (MgSO4). Removal of solvent gave 0.84 g (83%) of the title compound as a yellow oil: 1H-NMR (CDCl3) δ 7.41 (2H, d, J=8.3 Hz), 7.29 (2H, d, J=8.6 Hz), 7.10 (1H, d, J=1.8 Hz), 6.89 (1H, d, J=8.4 Hz), 6.63 (1H, dd, J=2.2, 8.4 Hz), 4.37 (2H, t, J=7.0 Hz), 3.05 82H, t, J=7.1 Hz), 2.79 (2H, q, J=7.5 Hz), 2.35 (2H, q, J=7.5 Hz), 1.33 (3H, t, J=7.50 Hz), 1.14 (3H, t, J=7.7 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 4 h
  3. filtrationfiltered through a pad of Celite
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue was dissolved in dichloromethane (200 mL)
  6. dry with materialdried (MgSO4)
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-5600f3ca94b24023933690e46924460d
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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