Sodium Methoxide → HCID 22726883, compound

HRID 2085966Notes

Reaction equation

HRID 2085966 reaction equation
[C:1]([S:4][C:5]1[S:9][C:8]([CH3:10])=[N:7][C:6]=1[CH2:11][S:12][C:13](=[O:15])[CH3:14])(=O)[CH3:2].C[O-].[Na+].ICC[S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:24])=[O:23]>CO>[C:13]([S:12][CH2:11][C:6]1[N:7]=[C:8]([CH3:10])[S:9][C:5]=1[S:4][CH2:1][CH2:2][S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:24])=[O:23])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 15885292(2-Iodoethanesulfonyl)benzeneHCID 22726749HCID 22726749, compound

Product 1

HCID 22726883HCID 22726883, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 5-acetylthio-4-acetylthiomethyl-2-methyl-1,3-thiazole (600 mg, 2.3 mmol) in methanol (10 mL) was dropwise added 0.5 M sodium methoxide in methanol (4.6 mL) at 0° C. and stirred at the same temperature for 30 min. 2-Iodoethyl phenylsulfone (620 mg, 2.1 mmol) was added and stirred for an additional 30 min. The solvent was removed and the residue was partitioned between water and ethyl acetate. The organic layer was concentrated and the residue was chromatographed (silica gel, dichloromethane), affording 800 mg of the title compound. 1H NMR (CDCl3) δ 2.30 (s, 3H), 2.64 (s, 3H), 3.00 (t, 2H), 3.30 (t, 2H), 4.23 (s, 2H), 7.58 (2H), 7.69 (1H), 7.89 (2H).

Workup

  1. customat 0° C.
  2. stirringstirred for an additional 30 min
  3. customThe solvent was removed
  4. customthe residue was partitioned between water and ethyl acetate
  5. concentrationThe organic layer was concentrated
  6. customthe residue was chromatographed (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-65945ae4b851496bae32eb26c8cba573
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

Loading…