Acetonitrile → HCID 12044346, Verbindung

HRID 1374931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1374931
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH2:7][OH:8].[Cl:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].C(#N)C>COC(C)(C)C>[Cl-:9].[C:13]1([C:11](=[O:12])[CH2:10][N+:3]2[C:2]([CH3:1])=[C:6]([CH2:7][OH:8])[S:5][CH:4]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 107572-ChloroacetophenoneHCID 10329317(4-Methyl-1,3-thiazol-5-yl)methanol

Produkt 1

HCID 12044346HCID 12044346, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

The neat reaction of 4-methyl-5-(hydroxymethyl)thiazole (590 mg, 4.57 mmol) and 2-chloroacetophenone (710 mg, 4.59 mmol) was heated at 110° C. The mixture solidified within 15 minutes. Acetonitrile (10 mL) was added and the mixture refluxed for another 3 hrs. It was cooled to room temperature and tert-butyl methyl ether (5 mL) was added and the reaction mixture was left overnight at room temperature. The product crystallized was filtered and washed well with a mixture of hexanes:EtOAc (1:1, v/v) and dried. It was recrystallized from a mixture of actonitrile/ethanol/tert-butyl methyl ether; yield 130 mg (10%); mp. 240–242° C. (dec.).

Aufarbeitung

  1. temperaturethe mixture refluxed for another 3 hrs
  2. temperatureIt was cooled to room temperature
  3. waitthe reaction mixture was left overnight at room temperature
  4. customThe product crystallized
  5. filtrationwas filtered
  6. washwashed well with a mixture of hexanes:EtOAc (1:1
  7. customv/v) and dried
  8. customIt was recrystallized from a mixture of actonitrile/ethanol/tert-butyl methyl ether

Quellen und Nachweise

ORD-Eintrag
ord-adad4e05cd404acaa5686a0d9d6b07bf
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07166625B2

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