1-Iodopropane → HCID 21504402, compound

HRID 1288303Notes

Reaction equation

HRID 1288303 reaction equation
[CH3:1][C:2]1[CH:10]=[C:6]([C:7]([NH2:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[CH2:12](I)[CH2:13][CH3:14]>[Na].C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][CH2:13][CH3:14])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 2

HCID 336431-IodopropaneHCID 107019875-MethylSalicylamide

Product 1

HCID 21504402HCID 21504402, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 5360545SodiumSolvent

Procedure

5-Methylsalicylamide (30.2 g; prepared as described in French Pat. No. M21) was dissolved in a solution of sodium (4.6 g.) in ethanol (200 ml.). Propyl iodide (37.4 g.) was added with stirring, and the mixture was stirred for 1 hour at room temperature and then under reflux for a further 19 hours. The mixture was concentrated to about 75 ml. and poured into water (300 ml.). The precipitated solid was filtered off and stirred with 2N sodium hydroxide solution (100 ml.). The insoluble solid was filtered off and washed with water to give crude 5-methyl-2-propoxybenzamide (37.5 g.), m.p. 112°-115° C.

Workup

  1. customprepared
  2. stirringthe mixture was stirred for 1 hour at room temperature
  3. temperatureunder reflux for a further 19 hours
  4. concentrationThe mixture was concentrated to about 75 ml
  5. additionand poured into water (300 ml.)
  6. filtrationThe precipitated solid was filtered off
  7. stirringstirred with 2N sodium hydroxide solution (100 ml.)
  8. filtrationThe insoluble solid was filtered off
  9. washwashed with water

Sources & evidence

ORD record
ord-9cd648c953054175ab2bf8a1afb66ed7
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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