Acetaminophen → N-[4-(4,6-Dichloro-pyrimidin-2-yloxy)-phenyl]-acetamide

HRID 225436

反応式

HRID 225436 の反応式
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[N:18]=[C:17](S(C)(=O)=O)[N:16]=1>C1COCC1.[NH4+].[Cl-].CCOC(C)=O>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[N:18]=[C:17]([O:11][C:8]2[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)[N:16]=1

参加物

7

反応物 3

HCID 1983AcetaminophenHCID 24758Sodium hydrideHCID 2396854,6-Dichloro-2-(methylsulfonyl)pyrimidine

生成物 1

HCID 57752793N-[4-(4,6-Dichloro-pyrimidin-2-yloxy)-phenyl]-acetamide収率 95.3%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

実験手順

A solution of 4-acetamidophenol (666 mg, 4.40 mmol) in anhydrous THF (40 ml), stirring at ambient temperature, was treated with a 60% dispersion of sodium hydride in mineral oil (176 mg, 4.40 mmol). The reaction mixture was then allowed to stir for 30 minutes at ambient temperature before 4,6-dichloro-2-methanesulfonyl-pyrimidine (1.0 g, 4.40 mmol) was added. The reaction was then allowed to stir for a further 3 hours before the reaction was diluted with saturated aqueous NH4Cl and EtOAc. The organic layer was separated, washed with saturated aqueous NaCl and dried over sodium sulfate then concentrated in vacuo. The residue was purified by column chromatography (Silica Gel, MeOH:CH2Cl2, 5:95) yield the title compound 1.25 g, (95%) as a solid. 1H-NMR (400 MHz, DMSO-d6): δ 2.06 (3 H, s), 7.18 (2 H, d, J=8.5 Hz), 7.62 (2 H, d, J=8.5 Hz), 10.05 (1 H, s), LC-MS: ES+=298.16, ES−=296.18).

後処理

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous NaCl
  4. dry with materialdried over sodium sulfate
  5. concentrationthen concentrated in vacuo
  6. customThe residue was purified by column chromatography (Silica Gel, MeOH:CH2Cl2, 5:95)

出典と根拠

ORDレコード
ord-c804fb4d8e134d36865990200ea5ae82
出典データセット
uspto-grants-2009_07
特許番号
US07557106B2

関連ノート

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