Ethyl Acetate → HCID 9907917、化合物

HRID 392530ノート

反応式

HRID 392530 の反応式
Br[CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:7](=[O:13])[NH:8][N:9]=[CH:10][C:11]=1[Cl:12].[CH3:14][NH:15][CH2:16][CH2:17][C:18]1[CH:27]=[CH:26][C:23]([O:24][CH3:25])=[C:20]([O:21][CH3:22])[CH:19]=1.C(=O)([O-])O.[K+].C(OCC)(=O)C>CC(C)=O.C(N(CC)CC)C>[Cl:12][C:11]1[CH:10]=[N:9][NH:8][C:7](=[O:13])[C:6]=1[NH:5][CH2:4][CH2:3][CH2:2][N:15]([CH2:16][CH2:17][C:18]1[CH:27]=[CH:26][C:23]([O:24][CH3:25])=[C:20]([O:21][CH3:22])[CH:19]=1)[CH3:14]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 77039N-Methylhomoveratrylamine2 回HCID 516893Potassium BicarbonateHCID 109344284-(3-bromopropylamino)-5-chloro-3(2H)-pyridazinone2 回

生成物 1

HCID 9907917HCID 9907917、化合物収率 59.1%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒2 回HCID 8471Triethylamine溶媒

実験手順

A mixture of 10.66 g (0.04 mole) of 4-(3-bromopropylamino)-5-chloro-3(2H)-pyridazinone (II), 10.0 g (0.05 mole) of N-methyl-homoveratryl amine (VI) and 8 g of potassium hydrogen carbonate is suspended in 80 cm3 of acetone. The reaction mixture is refluxed for 8 to 12 hours. The reaction is followed by TLC (eluent: ethyl acetate: acetone:triethylamine==10:10:0.5 (II Rf=0.76), (VI Rf=0.14), (I Rf=0.47)). The mixture is filtered while hot, washed with acetone and the mother liquor is evaporated in vacuo. To the residue 50 cm3 of ethyl acetate are added. The possibly separated inorganic substance is filtered off and the filtrate is evaporated again. The residual viscous, oily product (14 to 15 g) is triturated twice with 50 cm3 of hot water in order to remove the unreacted starting substance of the formula (VI). The warm aqueous solution is decanted. The oily residue is dissolved in methanol and dried over magnesium sulfate. Upon adding a small amount of diisopropyl ether and cooling the mixture white porous substance separates. Thus 9 g (59.0%) of crude product are obtained. M.p.: 89-90° C. After recrystallization from diisopropyl ether 7.0 g (46.0%) of the title compound are obtained.

後処理

  1. temperatureThe reaction mixture is refluxed for 8 to 12 hours
  2. filtrationThe mixture is filtered while hot,
  3. washwashed with acetone
  4. customthe mother liquor is evaporated in vacuo
  5. additionTo the residue 50 cm3 of ethyl acetate are added
  6. filtrationThe possibly separated inorganic substance is filtered off
  7. customthe filtrate is evaporated again
  8. customThe residual viscous, oily product (14 to 15 g) is triturated twice with 50 cm3 of hot water in order
  9. customto remove the
  10. customThe warm aqueous solution is decanted
  11. dissolutionThe oily residue is dissolved in methanol
  12. dry with materialdried over magnesium sulfate
  13. additionUpon adding a small amount of diisopropyl ether
  14. temperaturecooling the mixture white porous substance separates

出典と根拠

ORDレコード
ord-f6e5f7ce27df484783ef9ffb7433f8cc
出典データセット
uspto-grants-2004_10
特許番号
US06800758B1

反応ノート

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