Potassium Carbonate → 6-bromo-N-(2-(diethylamino)ethyl)phthalazin-1-amine

HRID 2357605노트

반응식

HRID 2357605 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][N:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([N:21]([CH2:25][CH3:26])[CH2:22][CH2:23][NH2:24])[CH3:20]>CN(C)C=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:24][CH2:23][CH2:22][N:21]([CH2:25][CH3:26])[CH2:19][CH3:20])=[N:7][N:6]=[CH:5]2

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 60993N,N-DiethylethylenediamineHCID 220304246-Bromo-1-chlorophthalazine

생성물 1

HCID 684546736-bromo-N-(2-(diethylamino)ethyl)phthalazin-1-amine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

6-Bromo-1-chlorophthalazine (0.22 g, 0.91 mmol) was dissolved in N,N-dimethylformamide (3 mL) and potassium carbonate (0.25 g, 1.81 mmol) and N1,N1-diethylethane-1,2-diamine (0.25 mL, 1.81 mmol) were added. The reaction mixture was heated to 80° C. for 5 h, cooled to ambient temperature and stirred for 16 h. The reaction mixture was diluted with 20 mL of EtOAc, added to an addition funnel and partitioned with sodium bicarbonate (saturated, aqueous). The organic layer was washed 3× with 20 mL of sodium bicarbonate (saturated, aqueous) and once with aqueous brine, separated, dried over sodium sulfate, and concentrated via rotovap to give crude product. The crude was purified by chromatography to obtain the title compound. Found MS (ES+): 323(M+H)+.

후처리

  1. temperaturecooled to ambient temperature
  2. additionadded to an addition funnel
  3. custompartitioned with sodium bicarbonate (saturated, aqueous)
  4. washThe organic layer was washed 3× with 20 mL of sodium bicarbonate (saturated, aqueous)
  5. customonce with aqueous brine, separated
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated via rotovap
  8. customto give crude product
  9. customThe crude was purified by chromatography

출처 및 근거

ORD 기록
ord-716d62a92dbf4913a5d22346c3782f3a
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759337B2

반응 노트

불러오는 중…