Acetic Acid → HCID 19032425, compound

HRID 266068Notes

Reaction equation

HRID 266068 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:37])[C:9]([N:12]2[C:16](=[O:17])[N:15]([C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:29][CH2:28][N:27]([C:30]5[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=5)[CH2:26][CH2:25]4)=[CH:20][CH:19]=3)[CH:14]=[N:13]2)([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[BH4-].[Na+].C(O)(=O)C>O1CCOCC1.CO.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:37])[C:9]([N:12]2[C:16](=[O:17])[N:15]([C:18]3[CH:19]=[CH:20][C:21]([N:24]4[CH2:25][CH2:26][N:27]([C:30]5[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=5)[CH2:28][CH2:29]4)=[CH:22][CH:23]=3)[CH:14]=[N:13]2)([CH3:11])[CH3:10])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 19032417HCID 19032417, compound

Product 1

HCID 19032425HCID 19032425, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-[2-(4-bromophenyl)-1,1-dimethyl-2-oxoethyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one (0.009 mol) and sodium tetrahydroborate (0.025 mol) in 1,4-dioxane (100 ml), methanol (30 ml) and water (50 ml) was stirred overnight. Acetic acid (5 ml) was added, followed by addition of water (500 ml). Crystallization resulted. The reaction mixture was stirred for 4 hours at room temperature. The precipitate was filtered off by suction (Buchner) and the solid was crystallized from 1-butanol. The precipitate was filtered off and dried, yielding 4.4 g (87%) of (±)-2-[2-(4-bromophenyl)-2-hydroxy-1,1-dimethylethyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one; mp. 224.5° C. (comp. 21).

Workup

  1. customCrystallization
  2. customresulted
  3. stirringThe reaction mixture was stirred for 4 hours at room temperature
  4. filtrationThe precipitate was filtered off by suction (Buchner)
  5. customthe solid was crystallized from 1-butanol
  6. filtrationThe precipitate was filtered off
  7. customdried

Sources & evidence

ORD record
ord-ff7ccba4f3074ccb877f637eed3dbb78
Source dataset
uspto-grants-1997_07
Patent number
US05650411

Reaction notes

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