Lithium iodide → HCID 10088818, compound

HRID 1296816Notes

Reaction equation

HRID 1296816 reaction equation
[CH:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][C:10]([NH:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([O-:18])=[O:17])=[S:11])=[CH:6][C:5]=1[CH3:24])([CH3:3])[CH3:2].[I-].[Li+]>N1C=CC=CC=1>[CH:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][C:10]([NH:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=[O:17])=[S:11])=[CH:6][C:5]=1[CH3:24])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 86606844HCID 86606844, compound

Product 1

HCID 10088818HCID 10088818, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-[2-(4-isopropyl-3-methyl-phenoxy)thioacetylamino]benzoate (0.50 g, 1.4 mmol) in pyridine (15 mL) was treated with anhydrous lithium iodide (1.87 g), and the resulting mixture was heated to reflux for 10 h. The solution was cooled and evaporated, and the residue was partitioned between 1 N aqueous HCl and ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and evaporated. The residual solid was purified by column chromatography to afford the title product (0.22 g, 0.64 mmol, 46%). m.p. 174–176° C. 1H NMR (CDCl3, 300 MHz): δ 9.84 (1H, br s), 8.39 (1H, t, J=2 Hz), 8.28 (1H, ddd, J=8, 2, 1 Hz), 8.00 (1H, dt, J=8, 2 Hz), 7.55 (1H, t, J=8 Hz), 7.19 (1H, d, J=8 Hz), 6.83–6.77 (2H, m), 4.97 (2H, s), 3.03 (1H, m, J=7 Hz), 2.32 (3H, s), 1.20 (6H, d, J=7 Hz). Mass spectrum (ES−): m/z 342. Elemental analysis: calculated for C19H21NO3S C, 66.45; H, 6.16; N, 4.08. observed C, 66.71; H, 6.65; N, 4.02.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 10 h
  3. temperatureThe solution was cooled
  4. customevaporated
  5. customthe residue was partitioned between 1 N aqueous HCl and ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residual solid was purified by column chromatography

Sources & evidence

ORD record
ord-0389909b0ed54fa488dda5784d0cdf26
Source dataset
uspto-grants-2007_07
Patent number
US07247741B2

Reaction notes

Loading…