Ammonia → HCID 18957900, compound

HRID 2379130Notes

Reaction equation

HRID 2379130 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N:15]3[C:19]4[CH:20]=[CH:21][C:22]([N+:24]([O-])=O)=[CH:23][C:18]=4[N:17]=[CH:16]3)[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[ClH:27].N>C(O)C>[ClH:27].[NH2:24][C:22]1[CH:21]=[CH:20][C:19]2[N:15]([C:11]3[CH:10]=[C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:14]=[CH:13][CH:12]=3)[CH:16]=[N:17][C:18]=2[CH:23]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 18957887HCID 18957887, compound

Product 1

HCID 18957900HCID 18957900, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(3'-methoxy-3-biphenylyl)-5-nitrobenzimidazole (1.5 g, 4.9 mmol), tin(ll)chloride (2.7 g), conc. hydrochloric acid (20 ml), and ethanol (10 ml) was refluxed for 2 hours and then neutralized by the addition of concentrated ammonia and filtered through celite. The filter cake was washed with ethanol and then methylene chloride. The phases of the filtrate were separated and the aqueous phase was extracted twice with methylene chloride. The combined organic phases were washed with water, dried and the product was precipitated as the hydrochloride. Yield: 1.5 g, 4.3 mmol, 88%. mp 195°-200° C. (decomposition).

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationfiltered through celite
  3. washThe filter cake was washed with ethanol
  4. customThe phases of the filtrate were separated
  5. extractionthe aqueous phase was extracted twice with methylene chloride
  6. washThe combined organic phases were washed with water
  7. customdried
  8. customthe product was precipitated as the hydrochloride

Sources & evidence

ORD record
ord-9dc3349166ba4a8b8b3efec2d60f0937
Source dataset
uspto-grants-1994_11
Patent number
US05360809

Reaction notes

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