Tetrachlorophthalic anhydride → 4,8-Dimethyl-6-(3,4,5,6-tetrachlorophthalimido)-quinaldine

HRID 26367

반응식

HRID 26367 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[C:7]([CH3:13])[CH:6]=[C:5]2[CH3:14].[Cl:15][C:16]1[C:26]([Cl:27])=[C:25]([Cl:28])[C:24]([Cl:29])=[C:18]2[C:19]([O:21][C:22](=O)[C:17]=12)=[O:20]>ClC1C=CC=CC=1Cl>[CH3:14][C:5]1[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=[C:2]([N:1]3[C:22](=[O:21])[C:17]4=[C:16]([Cl:15])[C:26]([Cl:27])=[C:25]([Cl:28])[C:24]([Cl:29])=[C:18]4[C:19]3=[O:20])[CH:3]=2)[N:8]=[C:7]([CH3:13])[CH:6]=1

참가 물질

4

반응물 2

HCID 8326Tetrachlorophthalic anhydrideHCID 213229336-Amino-4,8-dimethylquinaldine

생성물 1

HCID 213229214,8-Dimethyl-6-(3,4,5,6-tetrachlorophthalimido)-quinaldine수율 87%

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매

실험 절차

350 g of o-dichlorobenzene was added to 186 g (1.0 mole) of 6-amino-4,8-dimethylquinaldine and 286 g (1.0 mole) of 3,4,5,6-tetrachlorophthalic anhydride, and the mixture was refluxed at the boiling point for 4 hours. The reaction mixture was then cooled. The crystals precipitated were collected by filtration, and dried to afford 394 g (0.87 mole) of 4,8-dimethyl-6-(3,4,5,6-tetrachlorophthalimido)-quinaldine. Then, 372 g (1.30 moles) of 3,4,5,6-tetrachlorophthalic anhydride, 2,000 g of 1,2,4-trichlorobenzene and 40 g of anhydrous zinc chloride were added, and the mixture was heated under reflux for 3 hours. Then, 500 g of dimethylformamide was added, and the mixture was stirred under reflux for 1 hour. The product was treated in the same way as in paragraph (C) of Example 1 to afford 571 g (0.79 mole) of a yellow compound. Since the compound obtained was scarcely soluble in dimethylformamide, its visible spectrum could not be measured. In its infrared spectrum (KBr), absorptions ascribable to --CO--N--CO-- were observed at 1730 cm-1 and 1790 cm-1, and absorptions ascribable to --CO--C--CO--, at 1645 cm-1 and 1695 cm-1. The elemental analysis values of this product were as follows:

후처리

  1. temperaturethe mixture was refluxed at the boiling point for 4 hours
  2. temperatureThe reaction mixture was then cooled
  3. customThe crystals precipitated
  4. filtrationwere collected by filtration
  5. customdried

출처 및 근거

ORD 기록
ord-f4475bf8d0b549b580f6c77be305303e
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04150025

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