Water → HCID 12277508、化合物

HRID 1891038ノート

反応式

HRID 1891038 の反応式
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:5]2[CH2:4][C:3]1=[O:13].Br[CH2:15][CH2:16]Br.C([O-])([O-])=O.[K+].[K+].O>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.CN(C)C=O>[CH3:1][N:2]1[C:3](=[O:13])[C:4]2([CH2:16][CH2:15]2)[C:5]2[C:6](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:8]

参加物

7

反応物 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 3494362-Methylisoquinoline-1,3(2H,4H)-dione

生成物 1

HCID 12277508HCID 12277508、化合物収率 92%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
70 °C

実験手順

To a solution of N-methylhomophthalimide (4.05 kg), 1,2-dibromoethane (2.39 L), and Bu4NHSO4 (785 g) in N,N-dimethylformamide (32 L) were added K2CO3 (6.39 kg) and N,N-dimethylformamide (8.5 L) at room temperature. Then the solution was heated to 70° C., and was stirred for 2 hours at 68˜70° C. After cooling the reaction mixture to 40° C., water (81 L) was added. After the slurry was stirred for 1 hour at 40° C., it was allowed to cool to room temperature and was stirred overnight. The suspension was filtered, and the obtained wet crystal was washed with the mixture of N,N-dimethylformamide and water (N,N-dimethylformamide:water=1:1, 20 L), twice, and water (20 L), sequentially. It was dried at room temperature under N2 flow for several hours and then under the reduced pressure overnight to afford the title compound as pale pink crystal (4.67 kg, 4.30 kg assay, 92% yield).

後処理

  1. temperatureAfter cooling the reaction mixture to 40° C.
  2. stirringAfter the slurry was stirred for 1 hour at 40° C.
  3. temperatureto cool to room temperature
  4. stirringwas stirred overnight
  5. filtrationThe suspension was filtered
  6. washthe obtained wet crystal was washed with the mixture of N,N-dimethylformamide and water (N,N-dimethylformamide:water=1:1, 20 L)
  7. customIt was dried at room temperature under N2 flow for several hours

出典と根拠

ORDレコード
ord-7a0c645d69034a378ae9cc0eba811ae2
出典データセット
uspto-grants-2013_08
特許番号
US08507504B2

反応ノート

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