Ammonium Hydroxide → HCID 22557387, compound

HRID 984036Notes

Reaction equation

HRID 984036 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)([C:13]1[N:14]([CH3:18])[CH:15]=[CH:16][N:17]=1)O.Cl[Sn]Cl.[NH4+].[OH-]>CC(O)=O.Cl>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH:11]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:13]1[N:14]([CH3:18])[CH:15]=[CH:16][N:17]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 24479Stannous ChlorideHCID 22557408HCID 22557408, compound

Product 1

HCID 22557387HCID 22557387, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A mixture of (±)-α-(2-chloro-4-nitrophenyl)-α-(4-chlorophenyl)-1-methyl-1H-imidazole-2-methanol (0.0397 mol) and SnCl2 (0.2382 mol) in HOAc (150 ml) and HCl (150 ml) was stirred and refluxed for 2 hours, then cooled, poured out on ice, basified with NH4OH, filtered over celite and extracted with CH2Cl2 and CH3OH. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 12 g (91%) of (±)-3-chloro-4-[(4-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methyl]benzenamine (interm. 24).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperaturecooled
  3. additionpoured out on ice
  4. filtrationfiltered over celite
  5. extractionextracted with CH2Cl2 and CH3OH
  6. customThe organic layer was separated
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-dc3e9b2f0fb544a686edcf1f1ad6f1c0
Source dataset
uspto-grants-2005_03
Patent number
US06867207B2

Reaction notes

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