Diethyl Sulfate → HCID 12428626, compound

HRID 1679122Notes

Reaction equation

HRID 1679122 reaction equation
[CH2:1]([N:3]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[C:6](=[O:12])[C:5]2[CH:13]=[C:14]([CH3:16])[S:15][C:4]1=2)[CH3:2].C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:27][CH3:28])(=O)=O>CN(C)C=O>[CH2:1]([N:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:27][CH3:28])=[O:10])[C:6](=[O:12])[C:5]2[CH:13]=[C:14]([CH3:16])[S:15][C:4]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 30452477-Ethyl-2-methyl-4-oxo-4,7-dihydrothieno(2,3-b)pyridine-5-carboxylic acid

Product 1

HCID 12428626HCID 12428626, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 0.237 part of 7-ethyl-4,7-dihydro-2-methyl-4-oxothieno(2,3-b)pyridine-5-carboxylic acid and 0.83 part of pulverized potassium carbonate in 6 parts by volume of dry dimethylformamide is stirred under heating at 100° C for 1 hour. To the mixture is then added 0.3 part by volume of diethyl sulfate. The mixture is stirred under heating at 100° C for 1 hour and filtered to remove insoluble material. The filtrate is concentrated to dryness under reduced pressure and the residue is extracted with chloroform. Evaporation of the solvent from the extract 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.

Workup

  1. stirringThe mixture is stirred
  2. temperatureunder heating at 100° C for 1 hour
  3. filtrationfiltered
  4. customto remove insoluble material
  5. concentrationThe filtrate is concentrated to dryness under reduced pressure
  6. extractionthe residue is extracted with chloroform
  7. customEvaporation of the solvent from the extract

Sources & evidence

ORD record
ord-32c977785214447da012c422175bbb93
Source dataset
uspto-grants-1978_03
Patent number
US04079060

Reaction notes

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