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Ethyl Acetate → N-{4-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]phenyl}-N-methylmethanesulphonamide

HRID 256606
ノート
印刷プレビュー

反応式

HRID 256606 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[SH:14][C:15]1[CH:16]=[C:17]([C:21]2([O:27][CH3:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.[Cu]Cl.O>[CH3:28][O:27][C:21]1([C:17]2[CH:16]=[C:15]([S:14][C:2]3[CH:7]=[CH:6][C:5]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][CH:3]=3)[CH:20]=[CH:19][CH:18]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 13920676N-(4-Iodophenyl)-N-methylmethanesulphonamideHCID 193757154-(3-Mercaptophenyl)-4-methoxytetrahydropyran

生成物 1

HCID 19785586N-{4-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]phenyl}-N-methylmethanesulphonamide

試薬・触媒・溶媒 3

HCID 62652
Cuprous chloride
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

実験手順

A solution of N-(4-iodophenyl)-N-methylmethanesulphonamide (0.31 g, 1 mmol), 4-(3-mercaptophenyl)-4-methoxytetrahydropyran (0.22 g), potassium carbonate (20 mg) and copper (I) chloride (30 mg) in DMF (20 ml) was heated to 140° C. and stirred for 3 hours. Ethyl acetate (40 ml) and water (40 ml) were added and the mixture was filtered through celite. The filtrate was washed with water (40 ml) and brine (40 ml), dried (MgSO4) and the solvent evaporated. The product was purified by column chromatography, thus N-{4-[3-(4-methoxytetrahydropyran-4-yl)phenylthio]phenyl}-N-methylmethanesulphonamide was obtained as an oil (0.12 g, 42%). NMR Spectrum 1.85-2.10 (4H, m), 2.85 (3H, s) 3.00 (3H, s), 3.30 (3H, s), 3.75-3.90 (4H, m), 7.25-7.35 (8H, m).

後処理

  1. filtrationthe mixture was filtered through celite
  2. washThe filtrate was washed with water (40 ml) and brine (40 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated
  5. customThe product was purified by column chromatography

出典と根拠

ORDレコード
ord-19103a9c9d644555b7ad090d95e37f36
出典データセット
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05258399

反応ノート

読み込み中…

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