Sulfolane → HCID 15125489, compound

HRID 2106772Notes

Reaction equation

HRID 2106772 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:22])[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.S1(=O)(=O)CCCC1.C([N:32]([C:38]([O-])=[O:39])[N:33]=[CH:34]N(C)C)C>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:22]2[CH:34]=[N:33][NH:32][C:38]2=[O:39])[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

5

Reactant 3

HCID 31347SulfolaneHCID 15125488HCID 15125488, compoundHCID 86743987HCID 86743987, compound

Product 1

HCID 15125489HCID 15125489, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 54.3 parts of 3-bromo-4-[4-(4-methoxyphenyl)-1-piperazinyl]-benzenamine and 189 parts of tetrahydrothiophene 1,1-dioxide was added portionwise, during a 30 minutes-period, 28.6 parts of ethyl[(dimethylamino)methylene]hydrazinecarboxylate at 160° C. Upon completion, stirring and heating were continued at 170° C. till all ethanol was distilled off. After cooling to room temperature, 120 parts of 4-methyl-2-pentanone were added to dissolve the sticky residue. The whole was heated till a solution was obtained. After cooling, the supernatant phase was decanted and the residue was stirred in 2,2'-oxybispropane. The product was filtered off and dried, yielding 44.6 parts of 4-[3-bromo-4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (int. 34).

Workup

  1. temperatureheating
  2. distillationwas distilled off
  3. addition120 parts of 4-methyl-2-pentanone were added
  4. dissolutionto dissolve the sticky residue
  5. temperatureThe whole was heated till a solution
  6. customwas obtained
  7. temperatureAfter cooling
  8. customthe supernatant phase was decanted
  9. stirringthe residue was stirred in 2,2'-oxybispropane
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-8c8eb1bdc06047fda7b5f930ca7a0547
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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