Chloroform → 3-Chloro-5-methyl-8-thia-4,6-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2,4,6-tetraene

HRID 1013866

Reaktionsgleichung

Reaktionsgleichung von HRID 1013866
[CH3:1][C:2]1[NH:3][C:4](=O)[C:5]2[C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=3[S:8][C:6]=2[N:7]=1.O=P(Cl)(Cl)[Cl:18].C(Cl)(Cl)Cl>C(OC(=O)C)(=O)C>[Cl:18][C:4]1[C:5]2[C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=3[S:8][C:6]=2[N:7]=[C:2]([CH3:1])[N:3]=1

Komponenten

5

Edukt 3

HCID 6212ChloroformHCID 24813Phosphorus oxychlorideHCID 2093955-Methyl-8-thia-4,6-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2(7),5-trien-3-one

Produkt 1

HCID 2902373-Chloro-5-methyl-8-thia-4,6-diazatricyclo[7.4.0.0,2,7]trideca-1(9),2,4,6-tetraeneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

To a 50 mL flask was added 5 (220 mg, 1 mmol) and 5 mL POCl3. The resulting mixture was refluxed for 2 h, and the solvent was removed under reduced pressure to afford a dark residue. To this was added 30 mL of CHCl3 and 300 mg of silica gel. The solvent was evaporated to afford a plug Column chromatography of the plug with hexane:acetyl acetate=20:1 as eluent afford 192 g (81%) of 6 as a yellow solid: 1H NMR (DMSO-d6) δ 1.82 (m, 4H), 2.63 (s, 3H), 2.84 (m, 2H), 2.96 (m, 2H).

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 2 h
  2. customthe solvent was removed under reduced pressure
  3. customto afford a dark residue
  4. customThe solvent was evaporated
  5. customto afford a plug Column chromatography of the plug with hexane

Quellen und Nachweise

ORD-Eintrag
ord-cd92b0abf1bc41c68f3989a8a40faeb5
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07982035B2

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