Oxalyl chloride → 1,1-Dimethylethyl 2-[3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxo-2-propenyl]hydrazinecarboxylic acid

HRID 466047

反応式

HRID 466047 の反応式
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]([C:11]1[CH:12]=[C:13]([CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=1[OH:22])[CH:14]=[CH:15][C:16]([OH:18])=O)([CH3:10])[CH3:9].[CH3:27][C:28]([N:31]([C:33]([OH:35])=[O:34])[NH2:32])([CH3:30])[CH3:29]>C(Cl)Cl.CN(C)C=O>[CH3:27][C:28]([N:31]([C:33]([OH:35])=[O:34])[NH:32][C:16](=[O:18])[CH:15]=[CH:14][C:13]1[CH:12]=[C:11]([C:8]([CH3:7])([CH3:10])[CH3:9])[C:21]([OH:22])=[C:20]([C:23]([CH3:25])([CH3:24])[CH3:26])[CH:19]=1)([CH3:30])[CH3:29]

参加物

6

反応物 3

HCID 65578Oxalyl chlorideHCID 998193-(3,5-Ditert-butyl-4-hydroxyphenyl)prop-2-enoic acidHCID 219636841,1-Dimethylethyl hydrazinecarboxylic acid

生成物 1

HCID 543996901,1-Dimethylethyl 2-[3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxo-2-propenyl]hydrazinecarboxylic acid収率 76%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

Oxalyl chloride (2.9 g, 0.023 mole) is added dropwise to a stirred 0° C. solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxycinnamic acid (4.3 g, 0.016 mole) in methylene chloride (30 ml) and N,N-dimethylformamide (0.5 ml . After one hour the solvent is removed in vacuo. The residue is dissolved in methylene chloride (30 ml) and added dropwise to a stirred 0° C. solution of 1,1-dimethylethyl hydrazinecarboxylic acid (4.5 g, 0.034 mole). After the addition is complete, the mixture is allowed to warm to room temperature and stir 18 hours. The mixture is concentrated in vacuo and the residue dissolved in methylene chloride (50 ml) and washed with aqueous 2M HCl, saturated aqueous NaCl, and dried MgSO4. Filtration and concentration gives a solid which was recrystallized from ethyl acetate/isopropyl ether to provide 4.6 g (6.1 g theor., 76%) of 1,1-dimethylethyl 2-[3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxo-2-propenyl]hydrazinecarboxylic acid, mp 184° C.

後処理

  1. customAfter one hour the solvent is removed in vacuo
  2. dissolutionThe residue is dissolved in methylene chloride (30 ml)
  3. additionAfter the addition
  4. concentrationThe mixture is concentrated in vacuo
  5. dissolutionthe residue dissolved in methylene chloride (50 ml)
  6. washwashed with aqueous 2M HCl, saturated aqueous NaCl, and dried MgSO4
  7. filtrationFiltration and concentration
  8. customgives a solid which
  9. customwas recrystallized from ethyl acetate/isopropyl ether

出典と根拠

ORDレコード
ord-707515d2395246d390089bef73a5c9ef
出典データセット
uspto-grants-1992_10
特許番号
US05155122

関連ノート

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