Potassium Phosphate, Tribasic → HCID 86709396, compound

HRID 2172255Notes

Reaction equation

HRID 2172255 reaction equation
Cl[C:2]1[N:3]([CH2:10][CH2:11][CH:12]([OH:25])[CH2:13][O:14]S(C2C=CC(C)=CC=2)(=O)=O)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[O-]CC.[Na+].[F:30][C:31]([F:54])([F:53])[C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][N:40]2[CH2:45][CH2:44][N:43]([C:46]3[CH:51]=[CH:50][C:49](O)=[CH:48][CH:47]=3)[CH2:42][CH2:41]2)=[CH:34][CH:33]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.C(O)C>[N+:7]([C:5]1[N:6]=[C:2]2[N:3]([CH:4]=1)[CH2:10][CH2:11][CH:12]([CH2:13][O:14][C:49]1[CH:48]=[CH:47][C:46]([N:43]3[CH2:44][CH2:45][N:40]([CH2:39][CH2:38][C:35]4[CH:34]=[CH:33][C:32]([C:31]([F:30])([F:54])[F:53])=[CH:37][CH:36]=4)[CH2:41][CH2:42]3)=[CH:51][CH:50]=1)[O:25]2)([O-:9])=[O:8]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2723922Sodium ethoxideHCID 69482757HCID 69482757, compoundHCID 86709366HCID 86709366, compound

Product 1

HCID 86709396HCID 86709396, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Toluene-4-sulfonic acid 4-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxybutyl ester (1.12 g) was suspended in an ethanol (14 ml). An ethanol solution (1.13 ml) of 20% sodium ethoxide was added to the suspension, and the mixture was stirred at room temperature for 30 minutes. 4-{4-[2-(4-Trifluoromethylphenyl)ethyl]piperazin-1-yl}phenol (0.72 g) and tripotassium phosphate (0.61 g) were added to the reaction mixture and heated for 4 hours under reflux. After the reaction mixture was cooled to room temperature, water was added thereto, followed by extraction with methylene chloride. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→hexane:ethyl acetate=0:1) and recrystallized from methanol to afford the title compound as a pale yellow powder (0.72 g).

Workup

  1. temperatureheated for 4 hours
  2. temperatureunder reflux
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. extractionfollowed by extraction with methylene chloride
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0→hexane:ethyl acetate=0:1)
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-30b9a383d3b74296b56d8739130ae6dc
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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