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

HRID 466047노트

반응식

HRID 466047 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-707515d2395246d390089bef73a5c9ef
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155122

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