Benzyl Bromide → 5-(3,4-Dimethoxyphenyl)-2-benzylpyrazolin-3-one

HRID 1489654

반응식

HRID 1489654 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[NH:15][NH:14][C:13](=[O:16])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].N1[C:22]([CH3:23])=[CH:21][C:20](C)=[CH:19][C:18]=1[CH3:25].C(Br)C1C=CC=CC=1>C1(C)C=CC=CC=1.ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[NH:15][N:14]([CH2:25][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:13](=[O:16])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 79532,4,6-TrimethylpyridineHCID 220460885-(3,4-Dimethoxyphenyl)-pyrazolin-3-one

생성물 1

HCID 229023385-(3,4-Dimethoxyphenyl)-2-benzylpyrazolin-3-one

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

5 g of 5-(3,4-dimethoxyphenyl)-pyrazolin-3-one, prepared according to Example 1C, were suspended in 100 ml of toluene. First 3 ml of collidine and subsequently 3.6 ml of benzyl bromide were added dropwise to the suspension. After heating for 6 hours under reflux, the reaction mixture was cooled, and the precipitated crystals were filtered out and washed with isopropanol. The crystals obtained were dissolved in dichloromethane and washed with 2M citric acid. The organic phase was dried with magnesium sulfate and concentrated. For purification the residue was recrystallized from isopropanol. 4 g of 5-(3,4-dimethoxyphenyl)-2-benzyl-pyrazolin-3-one were obtained having a melting point of 165° C.

후처리

  1. temperatureAfter heating for 6 hours
  2. temperatureunder reflux
  3. temperaturethe reaction mixture was cooled
  4. filtrationthe precipitated crystals were filtered out
  5. washwashed with isopropanol
  6. customThe crystals obtained
  7. washwashed with 2M citric acid
  8. dry with materialThe organic phase was dried with magnesium sulfate
  9. concentrationconcentrated
  10. customFor purification the residue
  11. customwas recrystallized from isopropanol

출처 및 근거

ORD 기록
ord-b9eec5786b4c43f888099167371f7d17
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05679699

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