(Chlorothio)formyl chloride → 5-(4-Benzyloxyphenyl)-[1,3,4]oxathiazol-2-one

HRID 453104

Reaktionsgleichung

Reaktionsgleichung von HRID 453104
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:19]([S:21]Cl)=[O:20]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]2[O:14][C:19](=[O:20])[S:21][N:15]=2)=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 75990(Chlorothio)formyl chlorideHCID 27264314-Benzyloxybenzamide

Produkt 1

HCID 595495255-(4-Benzyloxyphenyl)-[1,3,4]oxathiazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 4-benzyloxybenzamide (0.25 g, 1.10 mmol) in toluene (15 ml) was added chlorocarbonylsulfenyl chloride (0.18 ml, 2.20 mmol) and the resulting reaction mixture was refluxed at 90° C. overnight. After the completion of the reaction (TLC monitoring), the mixture was concentrated, added diethyl ether and washed twice with water, twice with 5% NaHCO3, again with water, and was then dried (Na2SO4), concentrated under vacuum to give the product (crude yield 0.310 g, 98%) that was used as such for the next step.

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 twice with water, twice with 5% NaHCO3, again with water
  6. dry with materialwas then dried (Na2SO4)
  7. concentrationconcentrated under vacuum
  8. customto give the product (crude yield 0.310 g, 98%) that

Quellen und Nachweise

ORD-Eintrag
ord-c25d00487cf4471eb6576890df02807b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492414B2

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