Water → HCID 19032389, compound

HRID 266066Notes

Reaction equation

HRID 266066 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[N:20]=[CH:19][C:18]([N:21]4[CH:25]=[N:24][NH:23][C:22]4=[O:26])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH:34]([CH2:44][CH3:45])[C:35]([C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)=[O:36].O>CC1C=CC=CC=1.CN(C)C=O.ClC(Cl)Cl>[Cl:43][C:40]1[CH:39]=[CH:38][C:37]([C:35]([CH:34]([N:23]2[C:22](=[O:26])[N:21]([C:18]3[CH:19]=[N:20][C:15]([N:12]4[CH2:11][CH2:10][N:9]([C:6]5[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=5)[CH2:14][CH2:13]4)=[CH:16][CH:17]=3)[CH:25]=[N:24]2)[CH2:44][CH3:45])=[O:36])=[CH:42][CH:41]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 14986891HCID 14986891, compoundHCID 15896015HCID 15896015, compound

Product 1

HCID 19032389HCID 19032389, compoundYield 80.4%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,4-dihydro-4-[6-[4-(4-methoxyphenyl)-1-piperazinyl]-3-pyridinyl]-3H-1,2,4-triazol-3-one (0.014 mol) and sodium carbonate (0.06 mol) in methylbenzene (30 ml) and N,N-dimethylformamide (70 ml) was stirred and refluxed. 2-Bromo-1-(4-chlorophenyl)-1-butanone (0.015 mol) in trichloromethane (20 ml) was added dropwise and the mixture was stirred and refluxed with a water separator for 1 hour. The mixture was filtered warm and the tiltrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2). The pure fractions were collected and evaporated. The residue was crystallized from 2-propanol, yielding 6 g (80%) of (±)-2-[1-(4-chlorobenzoyl)propyl]-2,4-dihydro-4-[6-[4-(4-methoxyphenyl)-1-piperazinyl]-3-pyridinyl]-3H-1,2,4-triazol-3-one; mp. 142.4° C. (comp. 1).

Workup

  1. temperaturerefluxed
  2. stirringthe mixture was stirred
  3. filtrationThe mixture was filtered
  4. temperaturewarm
  5. customthe tiltrate was evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2)
  7. customThe pure fractions were collected
  8. customevaporated
  9. customThe residue was crystallized from 2-propanol

Sources & evidence

ORD record
ord-a22561edabe44b7dac48689774d2ce01
Source dataset
uspto-grants-1997_07
Patent number
US05650411

Reaction notes

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