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Toluene → 2-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide

HRID 12142
ノート
印刷プレビュー

反応式

HRID 12142 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.[Cl:26][C:27]1[CH:38]=[C:31]2[C:32](OC(=O)[NH:36][C:30]2=[CH:29][CH:28]=1)=[O:33]>O1CCCC1>[NH2:36][C:30]1[CH:29]=[CH:28][C:27]([Cl:26])=[CH:38][C:31]=1[C:32]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1)=[O:33]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1140TolueneHCID 661742-Amino-5-chloropyridineHCID 784805-Chloroisatoic anhydrideHCID 3251421Potassium bis(trimethylsilyl)amide

生成物 1

HCID 219064182-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide収率 99%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 2-amino-5-chloropyridine (787 mg, 6.1 mmol) in tetrahydrofuran (5 ml) was added 0.5M potassium bis(trimethylsilyl)amide in toluene (20 ml, 10.1 mmol) dropwise at −78° C. After stirred for additional 0.5 hr at −78° C., the mixture was added 5-chloroisatoic anhydride (1 g, 5.1 mmol) at −78° C. The mixture was warmed up to r.t gradually and stirred overnight. After concentrated, the crude was washed with saturated ammonium chloride solution and extracted by ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to give (2-amino-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide as yellow solid (1.39 g, 99%). MS found for C12H9Cl2N3O M+=282, (M+2)+=284.

後処理

  1. temperatureThe mixture was warmed up
  2. stirringstirred overnight
  3. concentrationAfter concentrated
  4. washthe crude was washed with saturated ammonium chloride solution
  5. extractionextracted by ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-77362edf322045e8a72f238e86be1f41
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07727982B2

反応ノート

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