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

HRID 12151
ノート
印刷プレビュー

反応式

HRID 12151 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 100%

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 (328 mg, 2.55 mmol) in tetrahydrofuran (5 ml) was 0.5M potassium bis(trimethylsilyl)amide in toluene (10 ml, 5.05 mmol) dropwise at −78° C. After stirred for additional 0.5 hr at −78° C., the mixture was added 5-chloroisatoic anhydride (0.5 g, 2.55 mmol) at −78° C. The mixture was warmed up to r.t gradually and stirred overnight. After quenched by saturated ammonium chloride solution, the mixture was 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 (0.71 g. 100%). MS found for C12H9Cl2N3O M+=282, (M+2)+=284.

後処理

  1. customdropwise at −78° C
  2. temperatureThe mixture was warmed up
  3. stirringstirred overnight
  4. customAfter quenched by saturated ammonium chloride solution
  5. extractionthe mixture was extracted 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-a9b6035cb27d4c51a725621d2aa97cec
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07727981B2

反応ノート

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