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

HRID 225436

반응식

HRID 225436 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c804fb4d8e134d36865990200ea5ae82
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557106B2

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