Phenylglyoxylic Acid → HCID 86755069, compound

HRID 849795Notes

Reaction equation

HRID 849795 reaction equation
[C:1]([NH:5][NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:15](C(O)=O)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CS(Cl)(=O)=O.[C:31](=O)(O)[O-:32].[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[C:1]([N:5]([C:31](=[O:32])[CH:21]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=[C:15]=[O:22])[NH:6][C:7](=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 11915Phenylglyoxylic AcidHCID 31297Methanesulfonyl chlorideHCID 299436N'-tert-butylbenzohydrazideHCID 516892Sodium Bicarbonate

Product 1

HCID 86755069HCID 86755069, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8471TriethylamineSolvent

Procedure

N'-t-butyl-N-benzoylhydrazine (1 g), benzoyl formic acid (1 g), and methanesulfonyl chloride (0.7 g) were stirred in toluene (35 ml) and saturated sodium bicarbonate (15 ml) at approximately 5° C. Triethylamine was added slowly, dropwise to the reaction mixture, and slowly warmed to room temperature. After stirring for 1 hour, the reaction mixture was diluted with toluene (20 ml) and the organic layer was washed several times with water. The organic layers were dried over magnesium sulfate, filtered and the toluene rotavapped off to afford a white gum. The crude product was chromatographed on silica gel (G:230-400 mesh) using a methylene chloride ether solvent system as eluent to afford a 65% yield of a white solid.

Workup

  1. customat approximately 5° C
  2. washthe organic layer was washed several times with water
  3. dry with materialThe organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customto afford a white gum
  6. customThe crude product was chromatographed on silica gel (G:230-400 mesh)

Sources & evidence

ORD record
ord-fb60c72b91c949328c6bda40445a79f8
Source dataset
uspto-grants-2000_01
Patent number
US06013836

Reaction notes

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