Potassium Iodide → 5-Chloro-2-propoxybenzamide

HRID 1460978Notes

Reaction equation

HRID 1460978 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 94528845-Chloro-2-propoxybenzamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-28af009435194eb6bf88e957b6f73117
Source dataset
uspto-grants-1991_12
Patent number
US05073559

Reaction notes

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