Dimethyl Sulfoxide → HCID 15125490, compound

HRID 2106773Notes

Reaction equation

HRID 2106773 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:22]2[CH:26]=[N:25][NH:24][C:23]2=[O:27])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1.CS(C)=O.[OH-].[K+].Br[CH:35]([CH2:37][CH3:38])[CH3:36]>O>[Br:1][C:2]1[CH:3]=[C:4]([N:22]2[CH:26]=[N:25][N:24]([CH:35]([CH3:36])[CH2:37][CH3:38])[C:23]2=[O:27])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65542-BromobutaneHCID 14797Potassium HydroxideHCID 15125489HCID 15125489, compound

Product 1

HCID 15125490HCID 15125490, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 45 parts of 4-[3-bromo-4-[4-(4-methoxyphenyl)-1-piperazinyl]-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one and 90 parts of dimethyl sulfoxide were added 15 parts of potassium hydroxide (pulverized). Then there were added 6.2 parts of 2-bromobutane and the whole was stirred for 20 hours at room temperature. The reaction mixture was poured into water. The produce was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of methylbenzene and hexane (1:2 by volume). The precipitated product was filtered off and recrystallized from 80 parts of methanol. The product was filtered off and dried in vacuo at 60° C., yielding a first fraction of 14.7 parts (29.8%) of 4-[3-bromo-4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one; mp. 144.6° C. The less pure fractions were collected and the eluent was evaporated. The residue was further purified by column chromatography (HPLC) over silica gel using a mixture of ethyl acetate and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from methanol, yielding a second fraction of 4-[3-bromo-4-[4-(4-methoxyphenyl)-1-piperazinyl]-phenyl]-2,4-dihydro-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one; mp. 144.7° C. (int. 35).

Workup

  1. extractionThe produce was extracted with trichloromethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from a mixture of methylbenzene and hexane (1:2 by volume)
  10. filtrationThe precipitated product was filtered off
  11. customrecrystallized from 80 parts of methanol
  12. filtrationThe product was filtered off
  13. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-cdd589d1d3a1413fb12be9761e4f9919
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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