Phenylglyoxylic Acid → N'-t-butyl-N'-benzoylcarbonyl-N-benzoylhydrazine

HRID 21665

Reaction equation

HRID 21665 reaction equation
C([N:5]([C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6])(C)(C)C.[C:15]([C:23]([OH:25])=O)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CS(Cl)(=O)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[C:8]([N:6]([C:23]([C:15](=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:25])[NH:5][C:7](=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:13])([CH3:9])[CH3:7]

Participants

7

Reactant 4

HCID 11915Phenylglyoxylic AcidHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 1275961N-(tert-butyl)benzohydrazide

Product 1

HCID 19368006N'-t-butyl-N'-benzoylcarbonyl-N-benzoylhydrazineYield 70%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8471TriethylamineSolvent

Procedure

N'-t-butyl-N'-benzoylhydrazine (1 g), benzoyl formic acid (0.7 g) and methanesulfonyl chloride (0.7 g) were stirred in toluene (30 ml) and saturated sodium bicarbonate (10 ml) at approximately 5° C. Triethylamine was added slowly, dropwise to the reaction mixture and stirred 1 hour at room temperature. After stirring for 1 hour, the reaction mixture was diluted with toluene (25 ml) and washed with water several times. The organic layers were dried over magnesium sulfate, filtered and the toluene rotavapped off to afford a white solid. After column chromatography, the product was obtained as a white solid in approximately 70% yield.

Workup

  1. customat approximately 5° C
  2. stirringAfter stirring for 1 hour
  3. washwashed with water several times
  4. dry with materialThe organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customto afford a white solid
  7. customAfter column chromatography, the product was obtained as a white solid in approximately 70% yield

Sources & evidence

ORD record
ord-8c3ff157d51443f48a219a96f1d4bdcc
Source dataset
uspto-grants-1995_06
Patent number
US05424333

Linked notes

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