2-Amino-5-chloropyridine → 4-chloro-N-(5-chloropyridin-2-yl)-3-nitrobenzamide

HRID 605212

반응식

HRID 605212 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=2)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

참가 물질

5

반응물 3

HCID 661742-Amino-5-chloropyridineHCID 81531DiisopropylethylamineHCID 1234774-Chloro-3-nitrobenzoyl chloride

생성물 1

HCID 6930954-chloro-N-(5-chloropyridin-2-yl)-3-nitrobenzamide수율 42.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 4-chloro-3-nitrobenzoyl chloride (1.00 g, 4.99 mmol) in dry methylene chloride (20 mL) under a nitrogen atmosphere was treated with 2-amino-5-chloropyridine (643 mg, 4.99 mmol) and N,N-diisopropylethylamine (1.05 mL, 6.00 mmol), and the resulting mixture stirred at room temperature for 18 hours. The solvent was removed by rotary evaporation in vacuo, the residue taken up in ethyl acetate (100 mL), and washed with saturated aqueous sodium bicarbonate (50 mL), water (2×50 mL), and brine (50 mL). The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Trituration with 5% ethyl acetate/methylene chloride afforded the title compound as a dark yellow solid (660 mg, 42%).

후처리

  1. customThe solvent was removed by rotary evaporation in vacuo
  2. washwashed with saturated aqueous sodium bicarbonate (50 mL), water (2×50 mL), and brine (50 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d9fc8539c0fc4485a34f45d554db6fb9
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910595B2

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