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

HRID 81708

反応式

HRID 81708 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8076Glycol monoethyl ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-2dec037877b041599ed4cd165660a167
出典データセット
uspto-grants-2014_09
特許番号
US08846704B2

関連ノート

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