(Chlorothio)formyl chloride → 5-(4-Methoxyphenyl)-1,3,4-oxathiazol-2-one

HRID 453089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453089
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][CH:4]=1.Cl[C:13]([S:15]Cl)=[O:14]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[O:8][C:13](=[O:14])[S:15][N:9]=2)=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 75990(Chlorothio)formyl chlorideHCID 769594-Methoxybenzamide

Produkt 1

HCID 8194565-(4-Methoxyphenyl)-1,3,4-oxathiazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-methoxybenzamide (0.30 g, 1.10 mmol) in toluene (10 ml) was added chlorocarbonylsulfenyl chloride (0.80 ml, 9.92 mmol). The resulting reaction mixture was refluxed at 80° C. for 3 h. After the completion of the reaction (TLC monitoring), the mixture was concentrated, added diethyl ether and washed with twice with water, twice with 5% NaHCO3, again with water, and was dried (Na2SO4), concentrated under vacuum to give the product (crude yield 0.475 g) that was carried forward to the next step without further purification.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. concentrationthe mixture was concentrated
  4. additionadded diethyl ether
  5. washwashed with twice with water
  6. dry with materialtwice with 5% NaHCO3, again with water, and was dried (Na2SO4)
  7. concentrationconcentrated under vacuum
  8. customto give the product (crude yield 0.475 g) that
  9. customwas carried forward to the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-848742b7949449a7b4dacf7d6e2bf053
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492414B2

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