Sodium hydride → HCID 70873591, compound

HRID 2172267Notes

Reaction equation

HRID 2172267 reaction equation
[O-]CC.[Na+].Cl[C:6]1[N:7]([CH2:14][CH2:15][CH:16]([OH:29])[CH2:17][O:18]S(C2C=CC(C)=CC=2)(=O)=O)[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[N:10]=1.[Cl:30][C:31]1[CH:50]=[CH:49][C:34]([O:35][CH2:36][C:37]2[O:38][CH:39]=[C:40]([C:42]3[CH:47]=[CH:46][C:45](O)=[CH:44][CH:43]=3)[N:41]=2)=[CH:33][CH:32]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[H-].[Na+]>CN(C)C=O.O.C(O)C>[Cl:30][C:31]1[CH:50]=[CH:49][C:34]([O:35][CH2:36][C:37]2[O:38][CH:39]=[C:40]([C:42]3[CH:47]=[CH:46][C:45]([O:18][CH2:17][CH:16]4[O:29][C:6]5=[N:10][C:9]([N+:11]([O-:13])=[O:12])=[CH:8][N:7]5[CH2:14][CH2:15]4)=[CH:44][CH:43]=3)[N:41]=2)=[CH:33][CH:32]=1

Participants

9

Reactant 5

HCID 24758Sodium hydrideHCID 62657Potassium Phosphate, TribasicHCID 2723922Sodium ethoxideHCID 70873650HCID 70873650, compoundHCID 86709366HCID 86709366, compound

Product 1

HCID 70873591HCID 70873591, compoundYield 53.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

An ethanol solution (0.45 ml) of 20% sodium ethoxide was added to an ethanol solution (10 ml) of toluene-4-sulfonic acid 4-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxybutyl ester (0.52 g), and the mixture was stirred at room temperature for 30 minutes. 4-[2-(4-Chlorophenoxymethyl)oxazol-4-yl]phenol (0.40 g) and tripotassium phosphate (0.34 g) were added to the reaction mixture, and the resulting mixture was heated under reflux for 2 hours. Water was added thereto and the precipitated solid was collected by filtration and dried at 60° C. The residue thus obtained was dissolved in dimethylformamide (3 ml), and sodium hydride (53 mg) was added thereto, followed by stirring at room temperature for 1 hour. Water was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was dried over magnesium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:methanol=10:0→methylene chloride:methanol=9:1) to afford the title compound as a pale yellow powder (0.34 g).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. filtrationthe precipitated solid was collected by filtration
  4. customdried at 60° C
  5. customThe residue thus obtained
  6. stirringby stirring at room temperature for 1 hour
  7. extractionfollowed by extraction with methylene chloride
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationAfter filtering
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (methylene chloride:methanol=10:0→methylene chloride:methanol=9:1)

Sources & evidence

ORD record
ord-f49cb440ff7a40918f8fb2240a21f70a
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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