Phosphorus sulfide (P2S5) → Methyl 4-[5-(4-methoxyphenyl)thiazol-2-yl]benzoate

HRID 2270051

Reaktionsgleichung

Reaktionsgleichung von HRID 2270051
[CH3:1][O:2][C:3]([C:5]1[CH:24]=[CH:23][C:8]([C:9]([NH:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=O)=O)=[CH:7][CH:6]=1)=[O:4].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:26]>O1CCCC1>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[S:26][C:9]([C:8]3[CH:23]=[CH:24][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=3)=[N:11][CH:12]=2)=[CH:16][CH:17]=1

Komponenten

4

Edukt 2

HCID 14817Phosphorus sulfide (P2S5)2×HCID 136403692-(4-Methoxycarbonylbenzamido)-4'-methoxyacetophenone

Produkt 1

HCID 18331084Methyl 4-[5-(4-methoxyphenyl)thiazol-2-yl]benzoateAusbeute 126,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-methoxycarbonylbenzamido)-4′-methoxyacetophenone (4.0 g) in tetrahydrofuran (80 ml) was added phosphorus pentasulfide (3.53 g), and refluxed for 2.5 hours. The reaction mixture was additionally added phosphorus pentasulfide (1.0 g), and refluxed for 1 hour. The reaction mixture was filtered, and the filtrate was cooled, and poured into water (1200 ml), and stirred for 1 hour. The resulting precipitate was collected by filtration. The solids were slurried in acetonitrile, and collected by filtration to give methyl 4-[5-(4-methoxyphenyl)thiazol-2-yl]benzoate (3.26 g).

Aufarbeitung

  1. temperaturerefluxed for 2.5 hours
  2. temperaturerefluxed for 1 hour
  3. filtrationThe reaction mixture was filtered
  4. temperaturethe filtrate was cooled
  5. additionpoured into water (1200 ml)
  6. filtrationThe resulting precipitate was collected by filtration
  7. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-99b7e238345d4d3bb3731e3359940f36
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06331521B1

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