Sodium Iodide → 3-(4-Methoxybenzyloxycarbonyl)-2-methylthio-4-oxo-6,7,8-trifluoro-4H-1-benzothiopyran

HRID 5359

Reaction equation

HRID 5359 reaction equation
[C:1]([C:4]1[C:9](=[O:10])[C:8]2[CH:11]=[C:12]([F:17])[C:13]([F:16])=[C:14]([F:15])[C:7]=2[S:6][C:5]=1[S:18][CH3:19])([OH:3])=[O:2].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1.C(N(CC)CC)C.[I-].[Na+]>C(Cl)(Cl)Cl>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][O:2][C:1]([C:4]2[C:9](=[O:10])[C:8]3[CH:11]=[C:12]([F:17])[C:13]([F:16])=[C:14]([F:15])[C:7]=3[S:6][C:5]=2[S:18][CH3:19])=[O:3])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 197958433-Carboxy-2-methylthio-4-oxo-6,7,8-trifluoro-4H-1-benzothiopyran

Product 1

HCID 545282143-(4-Methoxybenzyloxycarbonyl)-2-methylthio-4-oxo-6,7,8-trifluoro-4H-1-benzothiopyranYield 32.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 50 mg (0.163 mmol) of the compound of Example 112 in 0.2 ml of chloroform were added 30.7 mg (0.196 mmol) of p-methoxybenzyl chloride, 16.5 mg (0.163 mmol) of triethylamine and 29.4 mg (0.196 mmol) of sodium iodide, and the mixture was stirred for 5 hours at room temperature, which was poured into ice-water and extracted with dichloromethane. The organic layer was washed with water and with saturated saline solution, dried over anhydrous sodium sulfate and concentrated. The residue was purified by means of silica gel column chromatography (CHCl3) to obtain 22.5 mg (0.0528 mmol) of title compound (yield 32%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water and with saturated saline solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by means of silica gel column chromatography (CHCl3)

Sources & evidence

ORD record
ord-650824152b5742c386e87f846affa28e
Source dataset
uspto-grants-1993_09
Patent number
US05244892

Linked notes

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