Potassium Carbonate → HCID 19599422, compound

HRID 609622Notes

Reaction equation

HRID 609622 reaction equation
C(O[CH:4](OCC)[CH2:5][S:6][C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)C.C(=O)([O-])[O-].[K+].[K+]>O>[S:6]1[C:7]2=[CH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]2[CH:4]=[CH:5]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 264059HCID 264059, compound

Product 1

HCID 19599422HCID 19599422, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A well stirred mixture of 2-(2,2-diethoxyethylmercapto)indole (1.5 g, 0.0057 mole) in polyphosphoric acid (30 g) was heated to 130° C. for 20 minutes, then allowed to cool to room temperature and the mixture diluted with water (300 ml). The resulting aqueous solution was basified by addition of solid potassium carbonate and then extracted with ethyl acetate (2×120 ml). The combined extracts were dried (Na2SO4), concentrated in vacuo and the residue chromatographed on silica gel eluting with 10% ether/60-80 petrol to afford the title compound as a white solid (0.56 g, 57%).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (2×120 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customthe residue chromatographed on silica gel eluting with 10% ether/60-80 petrol

Sources & evidence

ORD record
ord-8a3c7d0feecc4842baa61152711a9b8b
Source dataset
uspto-grants-1999_12
Patent number
US05998409

Reaction notes

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