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Sodium Iodide → HCID 14727034, Verbindung

HRID 329418
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 329418
Br.[CH3:2][C:3]1[S:4][CH:5]=[CH:6][N:7]=1.[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[N:9]1.C(N([CH:29]([CH3:31])[CH3:30])CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(Cl)Cl.CC(CC(C)C)=O>[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([N:17]2[CH2:18][CH2:19][N:20]([CH2:13][CH2:14][CH2:15][CH2:16][C:30]3[CH:29]=[CH:31][C:12]([C:6]4[N:7]=[C:3]([CH3:2])[S:4][CH:5]=4)=[CH:11][CH:10]=3)[CH2:21][CH2:22]2)=[N:9]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 86743643HCID 86743643, Verbindung

Produkt 1

HCID 14727034HCID 14727034, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6344DichloromethaneLösungsmittelHCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

To a 100 ml round-bottomed flask equipped with condenser and N2 inlet were added 1.43 g (4.11 mmol) 4-(4-chlorobutyl)phenyl)-2-methylthiazole hydrobromide, 0.90 g. (4.11 mmol) N-benzisothiazolylpiperazine, 0.72 g (4.11 mmol) diisopropylethyl amine, 0.87 g (8.22 mmol) sodium carbonate, 2 mg sodium iodide, and 40 ml methylisobutyl ketone. The reaction was refluxed 31 hours, cooled, filtered, and the filtrate evaporated. The residue was chromatographed on silica gel using ethyl acetate/methylene chloride as eluent to afford an oil, which was taken up in methylene chloride and precipitated by addition of ether saturated with HCl. The solid was filtered, washed with ether, dried briefly, then washed with a minimal amount of acetone and dried to afford a white solid, m.p. 207-212° C., 1.87 g (87.2%). NMR (DMSO-d6): 1.6-1.8 (m, 4H), 2.64 (t, 2H), 2.72 (s, 3H), 3.1-3.3 (m, 4H), 3.4-3.6 (m,4 H), 4.0 (d, 2H), 7.2-8.1 (m, 8H), 7.85 (s, 1H).

Aufarbeitung

  1. customTo a 100 ml round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 31 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customThe residue was chromatographed on silica gel
  7. customto afford an oil, which
  8. customprecipitated by addition of ether saturated with HCl
  9. filtrationThe solid was filtered
  10. washwashed with ether
  11. customdried briefly
  12. washwashed with a minimal amount of acetone
  13. customdried
  14. customto afford a white solid, m.p. 207-212° C., 1.87 g (87.2%)

Quellen und Nachweise

ORD-Eintrag
ord-ac41fa10cf124ce8b5ea981e51e856f6
Quelldatensatz
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04891375

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