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

HRID 747500노트

반응식

HRID 747500 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-f01dd3f2a6a247d5b8a6a0777f997a9f
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07396842B2

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