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

HRID 1679756

反応式

HRID 1679756 の反応式
[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

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 278451HCID 278451、化合物HCID 3016950(1-(3,4-Dichlorophenyl)ethyl)hydrazine

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-80e60b2a22f14e97a0d3b79f3f4fd89b
出典データセット
uspto-grants-1978_03
特許番号
US04081596

関連ノート

読み込み中…