p-Toluenesulfonic acid → 3-Amino-1-(alpha-methyl-3,4-dichlorobenzyl)-pyrazol-5-one

HRID 1679756

반응식

HRID 1679756 반응식
[CH3:1][CH:2]([NH:11][NH2:12])[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([Cl:10])[CH:4]=1.C([O:15][C:16](=O)[CH:17]=[C:18]([NH2:22])OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C.C(Cl)Cl>[NH2:22][C:18]1[NH:12][N:11]([CH:2]([CH3:1])[C:3]2[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([Cl:10])[CH:4]=2)[C:16](=[O:15])[CH:17]=1

참가 물질

6

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 278451beta-Aminobeta-ethoxyacrylic acid ethyl esterHCID 3016950(1-(3,4-Dichlorophenyl)ethyl)hydrazine

생성물 1

HCID 141513883-Amino-1-(alpha-methyl-3,4-dichlorobenzyl)-pyrazol-5-one

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 6344Dichloromethane용매

실험 절차

41 g of α-methyl-3,4-dichlorobenzylhydrazine, dissolved in absolute ethanol, were added dropwise to a solution of 31.8 g of β-amino-β-ethoxyacrylic acid ethyl ester and 1.5 g of p-toluenesulphonic acid in 150 ml of ethanol at room temperature under nitrogen gas. After stirring for 2 hours and standing overnight, the reaction solution was concentrated as far as possible on a rotary evaporator. The residue which remained was dissolved in 2 N sodium hydroxide solution. Any unconverted starting products or by-products were extracted with ether. The aqueous phase was then brought to pH 5 with acetic acid. The oil thereby produced was taken up in methylene chloride and the organic phase was dried over Na2SO4. After evaporating off the solvent, the reaction product crystallized out. It was recrystallized from methanol. Melting point 127°-129° C; yield 21 g (38.5% of theory).

후처리

  1. waitstanding overnight
  2. concentrationthe reaction solution was concentrated as far as
  3. custompossible on a rotary evaporator
  4. dissolutionThe residue which remained was dissolved in 2 N sodium hydroxide solution
  5. extractionwere extracted with ether
  6. customThe oil thereby produced
  7. dry with materialthe organic phase was dried over Na2SO4
  8. customAfter evaporating off the solvent
  9. customthe reaction product crystallized out
  10. customIt was recrystallized from methanol

출처 및 근거

ORD 기록
ord-80e60b2a22f14e97a0d3b79f3f4fd89b
출처 데이터셋
uspto-grants-1978_03
특허 번호
US04081596

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