Potassium Iodide → 5-Chloro-2-propoxybenzamide

HRID 1460978

Reaktionsgleichung

Reaktionsgleichung von HRID 1460978
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].Br[CH2:13][CH2:14][CH3:15].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:13][CH2:14][CH3:15])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 3480945-Chloro-2-hydroxybenzamide

Produkt 1

HCID 94528845-Chloro-2-propoxybenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A stirred mixture of 5-chloro-2-hydroxybenzamide (20 g), 1-bromopropane (13.4 ml), potassium iodide (2.49 g) and anhydrous potassium carbonate (24.15 g) in acetone (250 ml) was heated under reflux for 20 hours. The cooled reaction mixture was filtered and the filter cake was washed with acetone. The filtrate and washings were combined and evaporated under reduced pressure to yield a residue which was washed with water, dilute aqueous sodium hydroxide, water and with diethyl ether to yield a crude product (19.85 g). This was recrystallised from acetonitrile, partitioned between chloroform and dilute aqueous sodium hydroxide, and was recrystallised from ethanol to yield 5-chloro-2-propoxybenzamide (16.78 g).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. washthe filter cake was washed with acetone
  6. customevaporated under reduced pressure
  7. customto yield a residue which
  8. washwas washed with water, dilute aqueous sodium hydroxide, water and with diethyl ether
  9. customto yield a crude product (19.85 g)
  10. customThis was recrystallised from acetonitrile
  11. custompartitioned between chloroform and dilute aqueous sodium hydroxide
  12. customwas recrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-28af009435194eb6bf88e957b6f73117
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05073559

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