Hydrazine → HCID 178482848, compound

HRID 1634091Notes

Reaction equation

HRID 1634091 reaction equation
[CH3:1][N:2]([CH2:4][C:5]#[CH:6])[CH3:3].FC(I)(F)[C:9]([F:12])([F:11])[F:10].[O-]S(S([O-])=O)=O.[Na+].[Na+].C([O-])(O)=O.[Na+].[NH2:28][NH2:29]>CC#N.O.O.CCO>[CH3:1][N:2]([CH3:3])[C:4]1[NH:29][N:28]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:5]=1

Participants

9

Reactant 5

HCID 9321HydrazineHCID 9636IodopentafluoroethaneHCID 24489Sodium DithioniteHCID 81643N,N-DimethylpropargylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 178482848HCID 178482848, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of N,N-dimethylpropargyl amine (20 mmol) and perfluoroethyl iodide (20 mmol) in MeCN/H2O (35 mL, 4:3), cooled to 0° C., was added slowly a solution of Na2S2O4 (20 mmol) and NaHCO3 (20 mmol) in H2O (10 mL). After 20 minutes, volatile material was removed, and the residue was extracted with Et2O. The organic phase was washed with brine, dried over MgSO4, and evaporated to give the crude iodoalkene as a yellow oil (2.85 g, 43%). A mixture of the iodoalkene (8.5 mmol) and NH2NH2*H2O (42.5 mmol) in EtOH (13 mL,) was heated under reflux for 5 hours. The solvent was removed, and the residue was partitioned between NaHCO3 and CH2Cl2. The organic phase was washed with brine, dried over MgSO4, and evaporated to give 5-dimethylamino-3-trifluoromethylpyrazole (0.65 g, 40%).

Workup

  1. customvolatile material was removed
  2. extractionthe residue was extracted with Et2O
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto give the crude iodoalkene as a yellow oil (2.85 g, 43%)
  7. temperaturewas heated
  8. temperatureunder reflux for 5 hours
  9. customThe solvent was removed
  10. customthe residue was partitioned between NaHCO3 and CH2Cl2
  11. washThe organic phase was washed with brine
  12. dry with materialdried over MgSO4
  13. customevaporated

Sources & evidence

ORD record
ord-17429f53c0ce4727bf5b08d3485dcaae
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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