M-Phenylenediamine → N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamine

HRID 81708

반응식

HRID 81708 반응식
Cl[C:2]1[N:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[C:24]1([NH2:31])[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=1>C(OCCO)C.C(OCC)(=O)C>[C:9]1([S:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:30][C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([NH2:31])[CH:25]=3)[N:7]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 3

HCID 7935M-PhenylenediamineHCID 81531DiisopropylethylamineHCID 219952052-Chloro-4-(phenylthio)pyrimidine

생성물 1

HCID 68746426N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamine수율 42%

시약·촉매·용매 2

HCID 8076Glycol monoethyl ether용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred mixture of 2-chloro-4-(phenylthio)pyrimidine (300 mg, 1.35 mmol) and diisopropylethylamine (0.35 mL, 2.02 mmol) in 2-ethoxyethanol (2 mL), was added 1,3-phenylenediamine (291 mg, 2.70 mmol) in one portion. The whole was heated under reflux for 20 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (20 mL), washed with water and brine. The organic solution was dried (Na2SO4), concentrated in vacuo. The residue was flash chromatographed on silica gel using ethyl acetate:petroleum ether (20:80→0:50) as eluant to give the product (167 mg, 42%).

후처리

  1. temperatureThe whole was heated
  2. temperatureunder reflux for 20 hours
  3. washwashed with water and brine
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel

출처 및 근거

ORD 기록
ord-2dec037877b041599ed4cd165660a167
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846704B2

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