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Hydroxylamine → 3,4-Dichlorobenzylthioaceto-hydroxamic acid

HRID 261877
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 261877
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH2:5][CH2:6][C:7](O)=[S:8].OS(O)(=O)=O.ClC(Cl)C.[NH2:23][OH:24].C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH2:5][CH2:6][C:7]([NH:23][OH:24])=[S:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 787HydroxylamineHCID 1118Sulfuric AcidHCID 63651,1-DichloroethaneHCID 10942334Sodium MethoxideHCID 178526174HCID 178526174, Verbindung

Produkt 1

HCID 867361013,4-Dichlorobenzylthioaceto-hydroxamic acidAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

20.2 g (0.08 mol) of 3,4-dichlorobenzylthioacetic acid are esterified with 10 ml of methanol, 0.6 ml of concentrated H2SO4 and 100 ml of dichloroethane. The mixture is heated under reflux for 4 hours, washed with water and with dilute bicarbonate solution, and dried. The mixture is evaporated in vacuo. The oily residue, in methanol, is treated with a solution of hydroxylamine (0.1 mol) in the presence of 0.18 mol of sodium methylate. After leaving the reactants in contact overnight, the mixture is evaporated to dryness in vacuo, the residue is taken up in water, the mixture is filtered over charcoal and the filtrate is precipitated with 3 N HCl, the product is extracted with ether, the extract is dried and evaporated and the product is crystallised in diisopropyl ether. 15 g of the stated product are obtained (yield 71%). Melting point: 75°-76° C.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 4 hours
  3. washwashed with water and with dilute bicarbonate solution
  4. customdried
  5. customThe mixture is evaporated in vacuo
  6. customAfter leaving the reactants in contact overnight
  7. customthe mixture is evaporated to dryness in vacuo
  8. filtrationthe mixture is filtered over charcoal
  9. customthe filtrate is precipitated with 3 N HCl
  10. extractionthe product is extracted with ether
  11. customthe extract is dried
  12. customevaporated
  13. customthe product is crystallised in diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-89f8b58841cf466d92e0ab3460a0ba0b
Quelldatensatz
uspto-grants-1979_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04152458

Notizen zur Reaktion

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