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

HRID 21666

반응식

HRID 21666 반응식
C([NH:5][NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(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:7](=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:5][C:23]([C:15](=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:25])([CH3:13])([CH3:9])[CH3:7]

참가 물질

7

반응물 4

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

생성물 1

HCID 19367969N'-t-butyl-N-benzoylcarbonyl-N'-benzoylhydrazine수율 65%

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 8471Triethylamine용매

실험 절차

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 eluant to afford a 65% yield of a white solid.

후처리

  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)

출처 및 근거

ORD 기록
ord-5c1f70365848435ead7e43c74e189906
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424333

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