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

HRID 5359

反応式

HRID 5359 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-650824152b5742c386e87f846affa28e
出典データセット
uspto-grants-1993_09
特許番号
US05244892

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