Methyl iodide → HCID 19843285, compound

HRID 2352541Notes

Reaction equation

HRID 2352541 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[S:16][C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:14]=2[OH:17])[CH:9]=1.IC>CN(C)C=O.O>[Cl:7][C:8]1[S:16][C:15]2[C:14](=[O:17])[C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][N:11]([CH3:1])[C:10]=2[CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469568HCID 178469568, compound

Product 1

HCID 19843285HCID 19843285, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.56 g) was added to a stirred solution of ethyl 2-chloro-7-hydroxythieno[3,2-b]pyridine-6-carboxylate (1.1 g) in dry dimethylformamide (100 ml) at ambient temperature. After 5 minutes iodomethane (0.3 ml) was added to the mixture and stirring was continued for 18 hours. The mixture was stirred at 60° for 2 hours and then evaporated to dryness to give a residue which was dissolved in water (80 ml). The aqueous solution was extracted with dichloromethane (3×150 ml) and the combined extracts dried over anhydrous sodium sulphate and evaporated to give the novel compound ethyl 2-chloro-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate, m.p. 168°-171°.

Workup

  1. stirringThe mixture was stirred at 60° for 2 hours
  2. customevaporated to dryness
  3. customto give a residue which
  4. extractionThe aqueous solution was extracted with dichloromethane (3×150 ml)
  5. dry with materialthe combined extracts dried over anhydrous sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-04fb873fb833416a8a17e5bf00071c37
Source dataset
uspto-grants-1989_10
Patent number
US04877793

Reaction notes

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