Hydrogen Bromide → HCID 86750399, compound

HRID 1683163Notes

Reaction equation

HRID 1683163 reaction equation
[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([CH:8]([N:11]2[C:15](=[O:16])[N:14]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][N:26](C(OCC)=O)[CH2:25][CH2:24]4)=[CH:19][CH:18]=3)[CH:13]=[N:12]2)[CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Br>O>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:35]=[CH:34][C:5]([C:6]([CH:8]([N:11]2[C:15](=[O:16])[N:14]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]4)=[CH:19][CH:18]=3)[CH:13]=[N:12]2)[CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 53742075HCID 53742075, compound

Product 1

HCID 86750399HCID 86750399, compoundYield 157.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (±)-ethyl 4-[4-[2-[1-(4-chlorobenzoyl)propyl]-2,3-dihydro-3-oxo-4H-1,2,4-triazol-4-yl]phenyl]-1-piperazinecarboxylate (15 g) in a hydrobromic acid solution 48% in water (150 ml) was stirred and refluxed or 6 hours and then stirred overnight. The mixture was evaporated, the residue was dissolved in CH2Cl2 and washed with NaHCO3 /H2O. The organic layer was dried, filtered and the solvent evaporate&. The residue was dissolved in 2-propanol and crystallized into the hydrochloric acid salt (1:2) in 2-propanol. The precipitate was filtered off and recrystallized from CH3CN, yielding 7.9 g (2.2%) of (±)-2-[1-(4-chlorobenzoyl)propyl]-2,4-dihydro-4-[4-(1-piperazinyl)phenyl]-3H-1,2,4-triazol-3-one . dihydrochloride . monohydrate; mp. 175.9° C. (interm. 1).

Workup

  1. temperaturerefluxed or 6 hours
  2. stirringstirred overnight
  3. customThe mixture was evaporated
  4. dissolutionthe residue was dissolved in CH2Cl2
  5. washwashed with NaHCO3 /H2O
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. dissolutionThe residue was dissolved in 2-propanol
  9. customcrystallized into the hydrochloric acid salt (1:2) in 2-propanol
  10. filtrationThe precipitate was filtered off
  11. customrecrystallized from CH3CN

Sources & evidence

ORD record
ord-7cfd6402c69d4fedb0c8b65bf1e42bbb
Source dataset
uspto-grants-1997_06
Patent number
US05637592

Reaction notes

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