Iodoethane → HCID 53859167, compound

HRID 848744Notes

Reaction equation

HRID 848744 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[NH:20][C:19]2[C:10](=[C:11]3[C:16](=[C:17]([O:21][CH3:22])[CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)[C:9](=[O:23])[CH:8]=1)=[O:6].[CH2:24](I)[CH3:25]>CN(C)C=O>[CH3:3][O:4][C:5]([C:7]1[CH:8]=[C:9]([O:23][CH2:24][CH3:25])[C:10]2[C:19]([N:20]=1)=[CH:18][C:17]([O:21][CH3:22])=[C:16]1[C:11]=2[CH:12]=[CH:13][CH:14]=[N:15]1)=[O:6]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 54457780HCID 54457780, compound

Product 1

HCID 53859167HCID 53859167, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.2 g of sodium hydride (50% suspension in mineral oil) is added to a solution of 6.5 g of 6-methoxy-1-oxo-1,4-dihydro-4,7-phenanthroline-3-carboxylic acid methyl ester in 50 ml of absolute dimethylformamide, whilst stirring at 40° in an inert gas atmosphere. After 30 minutes the reaction mixture is allowed to cool to room temperature, 4.3 g of ethyl iodide are added in portions, the mixture is stirred for 6 hours, 200 ml of ice-water are added, the mixture is extracted by shaking with 50 ml of petroleum ether and then extracted three times with 200 ml of chloroform each time. The chloroform extracts are combined, washed with water, dried over sodium sulphate and concentrated by evaporation under reduced pressure. 1-ethoxy-6-methoxy-4,7-phenanthroline-3-carboxylic acid methyl ester is obtained which, after recrystallisation from ethanol, melts at 188°-190°.

Workup

  1. stirringthe mixture is stirred for 6 hours
  2. extractionthe mixture is extracted
  3. stirringby shaking with 50 ml of petroleum ether
  4. extractionextracted three times with 200 ml of chloroform each time
  5. washwashed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-166cea795d1d4fd29187174e26e45b33
Source dataset
uspto-grants-1981_10
Patent number
US04297358

Reaction notes

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