4-Bromophenacyl bromide → N-{4-(4-bromophenyl)-3-[3-(dimethylamino) propyl]thiazol-2(3H)-ylidene}aniline

HRID 896610ノート

反応式

HRID 896610 の反応式
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[S:8].Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=1)=O>C(O)C>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]2[N:6]([CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:16])[C:7](=[N:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[S:8][CH:18]=2)=[CH:22][CH:23]=1

参加物

4

反応物 2

HCID 74544-Bromophenacyl bromideHCID 1982459N-(3-(Dimethylamino)propyl)-N'-phenylthiourea

生成物 1

HCID 396126N-{4-(4-bromophenyl)-3-[3-(dimethylamino) propyl]thiazol-2(3H)-ylidene}aniline収率 59.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of N-[3-(dimethylamino)propyl]-N′-phenylthiourea (800 mg) obtained in Reference Example 3 as described below and 2-bromo-4′-bromoacetophenone (1.09 g) in ethanol (30 ml) was heated with reflux under nitrogen atmosphere. Nine hours thereafter, the reaction mixture was concentrated under reduced pressure, and to the residue was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol (50:1)), and crystallized from isopropyl alcohol to give the title compound (830 mg)

後処理

  1. customobtained in Reference Example 3
  2. temperaturewas heated
  3. temperaturewith reflux under nitrogen atmosphere
  4. concentrationNine hours thereafter, the reaction mixture was concentrated under reduced pressure
  5. additionto the residue was added a saturated aqueous sodium hydrogen carbonate solution
  6. extractionthe mixture was extracted with chloroform
  7. washThe organic layer was washed with a saturated brine
  8. dry with materialdried over sodium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (chloroform:methanol (50:1))
  11. customcrystallized from isopropyl alcohol

出典と根拠

ORDレコード
ord-38c3d74bbec3432893257e6eea0f34c1
出典データセット
uspto-grants-2005_07
特許番号
US06919361B2

反応ノート

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