Cesium carbonate → HCID 178526843, compound

HRID 2171257Notes

Reaction equation

HRID 2171257 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[CH:11]=[CH:10][N:9]=[N:8]1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.I[C:26]1[C:27]([OH:35])=[N:28][CH:29]=[C:30]([N+:32]([O-:34])=[O:33])[CH:31]=1>[Cu](I)I.O.CS(C)=O>[N+:32]([C:30]1[CH:31]=[C:26]([N:8]2[N:9]=[CH:10][CH:11]=[N:7]2)[C:27]([OH:35])=[N:28][CH:29]=1)([O-:34])=[O:33]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 178418936HCID 178418936, compoundHCID 178526840HCID 178526840, compound

Product 1

HCID 178526843HCID 178526843, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
155 °C

Procedure

Cesium carbonate (24.4 g), 1,2,3-triazole (4.35 ml), 2,2,6,6-tetramethyl-3,5-heptanedione (3.89 ml), and copper iodide (7.1 g) were added to a DMSO (100 ml) solution containing 3-iodo-5-nitropyridin-2-ol (10 g) in a nitrogen atmosphere, followed by stirring at 155° C. for 1 hour. The reaction solution was adjusted to room temperature and water was added to the reaction solution. An insoluble precipitate was removed by filtration. 1M hydrochloric acid (110 ml) was added to the resulting filtrate, followed by extraction with ethyl acetate. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, a small amount of ethyl acetate was added to the obtained residue, and insoluble matter was collected by filtration. A yellow solid mixture (4.86 g) of 5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridin-2-ol and 5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridin-2-ol was thus obtained.

Workup

  1. customwas adjusted to room temperature
  2. customAn insoluble precipitate was removed by filtration
  3. addition1M hydrochloric acid (110 ml) was added to the resulting filtrate
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layers were washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled away under reduced pressure
  8. additiona small amount of ethyl acetate was added to the obtained residue, and insoluble matter
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-db741b774bbc433baa14251d1bfd11be
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

Loading…