Water → HCID 66819976, Verbindung

HRID 1044780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1044780
[N:1]([CH2:4][C:5]1[N:6]=[C:7]([C:10](=[O:12])[CH3:11])[S:8][CH:9]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[C:10]([C:7]1[S:8][CH:9]=[C:5]([CH2:4][NH2:1])[N:6]=1)(=[O:12])[CH3:11]

Komponenten

5

Edukt 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 866647591-(4-(Azidomethyl)-thiazol-2-yl)-ethanone

Produkt 1

HCID 66819976HCID 66819976, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(4-chloromethyl-thiazol-2-yl)-ethanone (1.08 g, 6.13 mmol) in dry DMF (21 mL) and treated with NaN3 (1.20 g, 18.39 mmol) at 65° C. until completion of the reaction. The reaction mixture was then cooled down to rt and partitioned between EA and water. The layers were separated and the org. layer dried over MgSO4, filtered and concentrated under reduced pressure to give crude 1-(4-(azidomethyl)-thiazol-2-yl)-ethanone as a yellow oil. To a solution of the crude azide (200 mg, 1.10 mmol) in THF (6 mL) were added polymer-supported Ph3P (2.0 eq.) and water (2 mL). The reaction mixture was stirred at 60° C. until completion of the reaction, cooled down to rt and filtered. The filtrate was partitioned between EA and aq. sat. NaHCO3 and the layers separated. The org. layer was dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a brown oil after purification by FC (CH2Cl2-MeOH-Et3N). LC-MS-conditions 01: tR=0.26 min; [M+H]+=157.04.

Aufarbeitung

  1. temperaturecooled down to rt
  2. filtrationfiltered
  3. customThe filtrate was partitioned between EA and aq. sat. NaHCO3
  4. customthe layers separated
  5. dry with materiallayer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5574056662e74cab9d7b8ca3bb6bb27a
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563714B2

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