Potassium Iodide → Methyl 5-benzoylamino-5,6,7,8-tetrahydro-naphth-1-yl-oxyacetate

HRID 1608059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1608059
[C:1]([NH:9][CH:10]1[CH2:19][CH2:18][CH2:17][C:16]2[C:15]([OH:20])=[CH:14][CH:13]=[CH:12][C:11]1=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]([O:31][CH3:32])=[O:30].[I-].[K+]>CN(C)C=O>[C:1]([NH:9][CH:10]1[CH2:19][CH2:18][CH2:17][C:16]2[C:15]([O:20][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:14][CH:13]=[CH:12][C:11]1=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 140149555-Benzoylamino-1-hydroxy-5,6,7,8-tetrahydro-naphthalene

Produkt 1

HCID 14014967Methyl 5-benzoylamino-5,6,7,8-tetrahydro-naphth-1-yl-oxyacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

50 mmol of 5-benzoylamino-1-hyroxy-5,6,7,8-tetrahydro-naphthalene and 100 ml of anhydrous potassium potassium carbonate are stirred at 50° C. in 100 ml of absolute dimethylformamide for 20 minutes. A solution of 60 mmol of methyl chloroacetate and 25 mmol of potassium iodide in 25 ml dimethylformamide is added dropwise and the mixture is stirred at 50° C. for 6 to 8 hours. It is filtered under the influence of heat, the residue is rinsed thoroughly with ethyl acetate and the filtrate is evaporated. The residue is stirred in a mixture of 10% strength NaOH and ethyl acetate or tetrahydrofuran for 10 minutes. The ethyl acetate phase is extracted by shaking once with 10% strength NaOH, dried over Na2SO4 and evaporated. The residue is recrystallized from ethyl acetate.

Aufarbeitung

  1. filtrationIt is filtered under the influence
  2. temperatureof heat
  3. washthe residue is rinsed thoroughly with ethyl acetate
  4. customthe filtrate is evaporated
  5. stirringThe residue is stirred in a mixture of 10% strength NaOH and ethyl acetate or tetrahydrofuran for 10 minutes
  6. extractionThe ethyl acetate phase is extracted
  7. stirringby shaking once with 10% strength NaOH
  8. dry with materialdried over Na2SO4
  9. customevaporated
  10. customThe residue is recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b9c0ab04ff9e49c9b482ca914fd769d5
Quelldatensatz
uspto-grants-1989_09
Patentnummer
US04868331

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