Iodoethane → HCID 12428626, compound

HRID 1605974Notes

Reaction equation

HRID 1605974 reaction equation
[CH3:1][C:2]1[S:16][C:5]2=[N:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9]([OH:10])=[C:4]2[CH:3]=1.[H-].[Na+].[CH2:19](I)[CH3:20]>CN(C)C=O>[CH2:19]([N:6]1[CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9](=[O:10])[C:4]2[CH:3]=[C:2]([CH3:1])[S:16][C:5]1=2)[CH3:20]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178469715HCID 178469715, compound

Product 1

HCID 12428626HCID 12428626, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 0.237 part of ethyl 2-methyl-4-hydroxythieno-[2,3-b]pyridine-5-carboxylate, 5 parts by volume of dry dimethyl-formamide and 0.048 part of 50 % sodium hydride in mineral oil is heated at 70°C for 30 minutes, and 0.12 part by volume of ethyl iodide is added thereto. The mixture is heated at 70°C for 2 hours and the solvent is evaporated under reduced pressure. The residue is extracted with chloroform, and the extract is washed with saturated aqueous sodium chloride and dried over sodium sulfate. Evaporation of the solvent gives ethyl 7-ethyl-4,7-dihydro-2-methyl-4-oxothieno[2,3-b]pyridine-5-carboxylate as crystals. Recrystallization from ethyl acetate yields colorless plates melting at 140°-142°C. This product is identical with the product in Example 24.

Workup

  1. temperatureThe mixture is heated at 70°C for 2 hours
  2. customthe solvent is evaporated under reduced pressure
  3. extractionThe residue is extracted with chloroform
  4. washthe extract is washed with saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ad6a4ff3bad040f89326eb456529fb47
Source dataset
uspto-grants-1976_04
Patent number
US03951989

Reaction notes

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