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Water → 2-(7-Bromoheptylthio)pyrimidine

HRID 54914
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 54914
C(=O)([O-])[O-].[K+].[K+].[SH:7][C:8]1[N:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br.O>CN(C)C=O>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][S:7][C:8]1[N:13]=[CH:12][CH:11]=[CH:10][N:9]=1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 783091,7-DibromoheptaneHCID 178418793HCID 178418793, Verbindung

Produkt 1

HCID 199569852-(7-Bromoheptylthio)pyrimidineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

Potassium carbonate (9.95 g) was added to a solution of 2-mercaptopyrimidine (6.73 g) and 1,7-dibromoheptane (15.48 g) in N,N-dimethylformamide (85 ml). The mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), and then the solvent was distilled off under reduced pressure. The residual oil was subjected to column chromatography on silica gel and eluted with ethyl acetate-hexane (1:4, v/v) to obtain 2-(7-bromoheptylthio)pyrimidine (8.5 g) as an oil. This oil was dissolved in N,N-dimethylformamide (45 ml). Potassium phthalimide (5.44 g) was added to the solution, and the mixture was stirred at 100° C. for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4). The solvent was distilled off under reduced pressure to obtain N-[7-(2-pyrimidinylthio)heptyl]phthalimide (10.36 g, 48.6%) as an oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off under reduced pressure
  5. washeluted with ethyl acetate-hexane (1:4, v/v)

Quellen und Nachweise

ORD-Eintrag
ord-27020e8ea7234b37a8cdcb3966018d17
Quelldatensatz
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05624917

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