Mandelic acid hydrazide → HCID 22632809, compound

HRID 2416620Notes

Reaction equation

HRID 2416620 reaction equation
[C:1]([NH:11][NH2:12])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].O.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17](S(O)(=O)=O)=[CH:16][CH:15]=1>CN(C)C=O>[C:14]1([C:24]2[O:3][CH:2]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:1](=[O:10])[NH:11][N:12]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 73126Mandelic acid hydrazideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 22632809HCID 22632809, compoundYield 482.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Mandelic acid hydrazide (1.66 g) and trimethyl o-benzoate (1.82 g) were heated under stirring in dimethyl formamide (30 ml) at 120° C. for 12 hours in the presence of p-toluene sulfonate monohydrate (0.2 g). The solvent was evaporated, and the residue was partitioned between ethyl acetate (150 ml) and water (50 ml). The ethyl acetate layer was washed with water (50 ml×2) and brine (50 ml), and then dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel chromatography (ethyl acetate/hexane, 1:1), to give the title compound as a white powder (1.28 g, 51%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate (150 ml) and water (50 ml)
  3. washThe ethyl acetate layer was washed with water (50 ml×2) and brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resulting residue was purified by silica gel chromatography (ethyl acetate/hexane, 1:1)

Sources & evidence

ORD record
ord-5fac143e2add4eb0ad22222f0729e001
Source dataset
uspto-grants-2004_11
Patent number
US06825192B1

Reaction notes

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