Hydrogen Bromide → 3-[4-[4-(4-Hydroxyphenyl)-1-piperazinyl]phenyl]-5,5-dimethyl-1-(1-methyl-2-oxopropyl)-2,4-imidazolidinedione

HRID 414245Notes

Reaction equation

HRID 414245 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[C:25](=[O:26])[C:24]([CH3:28])([CH3:27])[N:23]([CH:29]([CH3:33])[C:30](=[O:32])[CH3:31])[C:22]4=[O:34])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.S(OS([O-])=O)([O-])=O.[Na+].[Na+].Br>O>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:16]=[CH:17][C:18]([N:21]4[C:25](=[O:26])[C:24]([CH3:27])([CH3:28])[N:23]([CH:29]([CH3:33])[C:30](=[O:32])[CH3:31])[C:22]4=[O:34])=[CH:19][CH:20]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24346Disodium disulfiteHCID 212819093-[4-[4-(4-Methoxyphenyl)-1-piperazinyl]phenyl]-5,5-dimethyl-1-(1-methyl-2-oxopropyl)-2,4-imidazolidinedione

Product 1

HCID 151255513-[4-[4-(4-Hydroxyphenyl)-1-piperazinyl]phenyl]-5,5-dimethyl-1-(1-methyl-2-oxopropyl)-2,4-imidazolidinedioneYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 25.6 parts of 3-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-5,5-dimethyl-1-(1-methyl-2-oxopropyl)-2,4-imidazolidinedione, 3 parts of sodium disulfite and 375 parts of a hydrobromic acid solution 48% in water was stirred for 6 hours at reflux temperature. After cooling. the crystallized product was filtered off, washed with 2-propanone and suspended in a mixture of water, trichloromethane and 1-butanol. The whole was treated with potassium carbonate (pH 8~9). The separated organic layer was set aside and the aqueous phase was extracted twice with the same mixture. The combined extracts (see above) were evaporated in vacuo. The residue was crystallized from 1-butanol. The product was filtered off and dried, yielding 21.3 parts (86%) of 3-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-5,5-dimethyl-1-(1-methyl-2-oxopropyl)-2,4-imidazolidinedione; mp. 225.9° C. (intermediate 21).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe crystallized product was filtered off
  4. washwashed with 2-propanone
  5. additionsuspended in a mixture of water, trichloromethane and 1-butanol
  6. additionThe whole was treated with potassium carbonate (pH 8~9)
  7. extractionthe aqueous phase was extracted twice with the same mixture
  8. customThe combined extracts (see above) were evaporated in vacuo
  9. customThe residue was crystallized from 1-butanol
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-302aa818216140e9ac0ca3dd19cd0fbc
Source dataset
uspto-grants-1988_12
Patent number
US04791111

Reaction notes

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