Water → HCID 178448862, compound

HRID 729990Notes

Reaction equation

HRID 729990 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[NH4+].[OH-].[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=1[C:19]1[NH:20][C:21]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[C:22]([C:24]2[N:29]=[C:28]([NH:30][CH2:31][CH:32]([CH3:34])[CH3:33])[C:27]([N+:35]([O-])=O)=[CH:26][CH:25]=2)[N:23]=1.O>C1COCC1.CCOC(C)=O>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=1[C:19]1[NH:20][C:21]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[C:22]([C:24]2[N:29]=[C:28]([NH:30][CH2:31][CH:32]([CH3:34])[CH3:33])[C:27]([NH2:35])=[CH:26][CH:25]=2)[N:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 178448863HCID 178448863, compound

Product 1

HCID 178448862HCID 178448862, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add sodium dithionite (2.58 g, 14.82 mmol) followed by 32% NH4OH (9 mL) to a solution of {6-[2-(2,6-dichlorophenyl)-5-phenyl-1H-imidazol-4-yl]-3-nitropyridin-2-yl}isobutylamine (1.43 g, 2.96 mmol) in 50 mL of 1:1 THF:water mixture. Stir the mixture at RT for 2 h. Dilute with EtOAc. Wash the organic layer with saturated aqueous NaCl and dry the organic phase over Na2SO4. Concentrate to yield the title compound (1.32 g, 98%).

Workup

  1. washWash the organic layer with saturated aqueous NaCl
  2. dry with materialdry the organic phase over Na2SO4
  3. concentrationConcentrate

Sources & evidence

ORD record
ord-360421208bf64e348f4cfa048c182e4d
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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