Hydrochloric Acid → HCID 57436867, compound

HRID 1723994Notes

Reaction equation

HRID 1723994 reaction equation
[SH:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:13])[C:11]=1[CH3:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:14](=O)([O-])[O-].[K+].[K+].IC.Cl>CC(C)=O.O>[CH3:12][C:11]1[C:10](=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:3][C:2]=1[S:1][CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57436868HCID 57436868, compound

Product 1

HCID 57436867HCID 57436867, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution containing 2-mercapto-3-methyl-chromen-4-one (2.26 g, 11.76 mmol) and potassium carbonate (1.62 g, 11.76 mmol) in acetone (120 mL) was added iodomethane (807 μL, 12.93 mmol). The reaction stirred under nitrogen atmosphere at room temperature for 16 hours before being concentrated to yield a crude oil. The residue was taken up in water and adjusted to pH 7 with 5% HCl. The resulting aqueous layer was washed with ethyl acetate. The the organic layer was then washed with water and brine, dried over sodium sulfate, filtered, and concentrated to obtain the desired product as a yellow solid (1.95 g, 80% yield), which was taken on to the next step without further purification. 1H NMR (600 MHz, CDCl3): δ 8.21 (d, 1H, J=6.6 Hz), 7.61 (m, 1H), 7.38 (m, 2H), 2.66 (s, 3H), 2.09 (s, 3H).

Workup

  1. concentrationbefore being concentrated
  2. customto yield a crude oil
  3. washThe resulting aqueous layer was washed with ethyl acetate
  4. washThe the organic layer was then washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-113ba621e48948e197926f8aa9b0212d
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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