Potassium ethylxanthate → HCID 178474659, compound

HRID 1661441Notes

Reaction equation

HRID 1661441 reaction equation
Cl.[NH2:2][C:3]1[C:11]([OH:12])=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])=[CH:5][CH:4]=1.[C:19](=S)(OCC)[S-:20].[K+]>N1C=CC=CC=1.C(OCC)(=O)C>[SH:20][C:19]1[O:12][C:11]2[C:10]3[CH:9]([CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])[CH2:8][CH2:7][C:6]=3[CH:5]=[CH:4][C:3]=2[N:2]=1

Participants

5

Reactant 2

HCID 2735045Potassium ethylxanthateHCID 67354374N-[2-(6-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide Hydrochloride

Product 1

HCID 178474659HCID 178474659, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[2-(6-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide hydrochloride (100 mg, 0.369 mmol) and potassium O-ethyl dithiocarbonate (65.1 mg, 0.406 mmol) were heated under reflux in pyridine (1 mL) for 2 hr. The reaction solution was diluted with ethyl acetate, washed with 1N hydrochloric acid and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→90/10) to give the title compound (64.8 mg, yield 64%).

Workup

  1. washwashed with 1N hydrochloric acid and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→90/10)

Sources & evidence

ORD record
ord-6c64fec8ae5a49dc830d7a5d69bba5fe
Source dataset
uspto-grants-2011_10
Patent number
US08030337B2

Reaction notes

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