1-Bromo-2-methylpropane → 4-carboxy-2-isobutyl-6-[4-(methylthio)phenyl)-2H-pyridazin-3-one

HRID 7993

反応式

HRID 7993 の反応式
C[O:2][C:3]([C:5]1[C:6](=[O:19])[NH:7][N:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)[CH:10]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[CH:27]([CH3:29])[CH3:28].C(=O)([O-])O.[Na+]>CN(C)C=O>[C:3]([C:5]1[C:6](=[O:19])[N:7]([CH2:26][CH:27]([CH3:29])[CH3:28])[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)[CH:10]=1)([OH:2])=[O:4]

参加物

6

反応物 4

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 219916864-methoxycarbonyl-6-[4-(methylthio)phenyl]-2H-pyridazin-3-one

生成物 1

HCID 219916394-carboxy-2-isobutyl-6-[4-(methylthio)phenyl)-2H-pyridazin-3-one収率 65.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-methoxycarbonyl-6-[4-(methylthio)-phenyl]-2H-pyridazin-3-one (8.00 g, 29.0 mmol) in N,N-dimethylformamide (80 mL) were added potassium carbonate (8.02 g, 58.0 mmol) and isobutyl bromide (4.76 g, 34.8 mmol), and the mixture was stirred at 80° C. for 2 hours. The temperature of the reaction mixture was allowed to drop back to room temperature, and a saturated aqueous solution of sodium hydrogencarbonate was added. The mixture was then extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off. Following the procedure of Example 1 (7), the residue was reacted to yield the title compound as a yellow solid [yield: 65.1% (2 steps)].

後処理

  1. customto drop back to room temperature
  2. extractionThe mixture was then extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was reacted

出典と根拠

ORDレコード
ord-91f9a9d242cc4d829d962d9a6373321d
出典データセット
uspto-grants-2006_08
特許番号
US07087606B2

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