2-Chloroaniline → HCID 901567, Verbindung

HRID 430510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 430510
[CH3:1][C:2]1O[C:4](=[O:11])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[Cl:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15]>C(O)(=O)C>[CH3:1][C:2]1[N:15]([C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[Cl:12])[C:4](=[O:11])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Komponenten

4

Edukt 2

HCID 72402-ChloroanilineHCID 126692502-Methyl-thieno[3,2-d][1,3]oxazin-4-one

Produkt 1

HCID 901567HCID 901567, VerbindungAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

2-Methyl-thieno[3,2-d][1,3]oxazin-4-one (1.67 g, 10 mmol) and o-chloroaniline (2.1 mL, 20 mmol) were combined in acetic acid (20 mL) and refluxed for 4.5 hours. The reaction was partitioned between ethyl acetate and water. The two phase mixture was treated with sodium bicarbonate until the aqueous layer was basic and the phases were then separated. The aqueous phase was extracted with ethyl acetate and the combined organic layer was washed with water and brine, dried over sodium sulfate and concentrated to leave a brown oil. This residue was purified by flash chromatography on silica gel (30×150 mm). Elution with 10% and 20% ethyl acetate/hexane gave 1.42 g (51%) of 2-methyl-3-(2-chlorophenyl)-3H-thieno[3,2-d]pyrimidin-4-one was isolated as a brown oil which solidified on standing.

Aufarbeitung

  1. temperaturerefluxed for 4.5 hours
  2. customThe reaction was partitioned between ethyl acetate and water
  3. additionThe two phase mixture was treated with sodium bicarbonate until the aqueous layer
  4. customthe phases were then separated
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe combined organic layer was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto leave a brown oil
  10. customThis residue was purified by flash chromatography on silica gel (30×150 mm)
  11. washElution with 10% and 20% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-e4a506b693d44a2f815dd5135123dcbb
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06323208B1

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