P-Toluenesulfonylhydrazide → HCID 21705612, compound

HRID 1596051Notes

Reaction equation

HRID 1596051 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH:12]=[CH:13][CH2:14][OH:15].C1(C)C=CC(S(NN)(=O)=O)=CC=1.O.O.O.C([O-])(=O)C.[Na+]>CN(C=O)C.O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][OH:15]

Participants

6

Reactant 3

HCID 15303P-ToluenesulfonylhydrazideHCID 23665404Sodium Acetate TrihydrateHCID 53695575HCID 53695575, compound

Product 1

HCID 21705612HCID 21705612, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of Example 3C (3.82 g, 14.5 mmol) in DMF and para-toluene- sulfonhydrazide (27 g, 145 mmol) was heated to reflux and treated with sodium acetate trihydrate (32.8 g, 241 mmol) in water (380 mL) over 3 hours. The mixture was allowed to stir at reflux for 2 hours, cooled, partitioned between CH2Cl2 and water. The organic layer was dried (Na2SO4), filtered, concentrated and purified on silica gel with a gradient of CH2Cl2 to 2% methanol/CH2Cl2 to provide 2.88 g (75%) of the desired compound as a pale yellow oil.

Workup

  1. temperatureto reflux
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. custompartitioned between CH2Cl2 and water
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified on silica gel with a gradient of CH2Cl2 to 2% methanol/CH2Cl2

Sources & evidence

ORD record
ord-abe57a290dc44c31aa1c50210dfe779e
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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