Hydrogen Bromide → HCID 23048852, compound

HRID 2106777Notes

Reaction equation

HRID 2106777 reaction equation
Br.S([O-])(O)=O.[Na+].[CH2:7]([N:11]1[C:16](=[O:17])[CH:15]=[N:14][N:13]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][C:33]([O:36]C)=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[C:12]1=[O:38])[CH2:8][CH2:9][CH3:10]>O.C(O)(=O)C>[CH2:7]([N:11]1[C:16](=[O:17])[CH:15]=[N:14][N:13]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:25][CH2:26][N:27]([C:30]4[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=4)[CH2:28][CH2:29]3)=[CH:20][CH:19]=2)[C:12]1=[O:38])[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 260Hydrogen Bromide2×HCID 23048861HCID 23048861, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 23048852HCID 23048852, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 300 parts of a hydrobromic acid solution 48% in water, 100 parts of a hydrobromic acid solution in acetic acid and 2 parts of sodium hydrogen sulfite were added 18.9 parts of 4-butyl-2-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione. Stirring was continued for 5 hours at reflux temperature. After cooling, the precipitated product was filtered off and dissolved in a mixture of water and methanol. The mixture was neutralized with a saturated sodium hydrogen carbonate solution. The precipitated product was filtered off and crystallized twice; first from 4-methyl-2-pentanone and then from 1-propanol. The product was filtered off and dried in vacuo at 75° C., yielding 9.1 parts (50.2%) of 4-butyl-2-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione; mp. 202.3° C. (compound 10.05).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe precipitated product was filtered off
  4. dissolutiondissolved in a mixture of water and methanol
  5. filtrationThe precipitated product was filtered off
  6. customcrystallized twice
  7. filtrationThe product was filtered off
  8. customdried in vacuo at 75° C.

Sources & evidence

ORD record
ord-c8cba22966e0407381d57b7148ffdb45
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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