Pyridine → 4-chloro-N-(5-chloropyridin-2-yl)-2-nitrobenzamide

HRID 644179

반응식

HRID 644179 반응식
[N+:1]([C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.N1C=CC=CC=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=1>ClCCl.CN(C=O)C>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([NH:26][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])=[N:28][CH:29]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 661742-Amino-5-chloropyridineHCID 804754-Chloro-2-nitrobenzoic acid

생성물 1

HCID 46550994-chloro-N-(5-chloropyridin-2-yl)-2-nitrobenzamide수율 74.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

To a stirring suspension of 2-nitro-4-chlorobenzoic acid (20 g, 99 mmol) in dichloromethane (500 mL) was added a few drops of DMF, followed by oxalyl chloride (15.1 g, 119 mmol). After 1 h, the solvent was removed in vacuo and the residue was dissolved in dichloromethane (500 mL). To this stirring solution was added pyridine (24 mL, 297 mmol) followed by 2-amino-5-chloropyridine (12.7 g, 99 mmol). After stirring overnight, the solvents were removed in vacuo and the residue was stirred vigorously with ethyl acetate and water for several hours. The mixture was filtered to give a white solid, which was washed with ethyl acetate and dried in vacuo to give 23 g (74%) of the title compound. The combined ethyl acetate washings and extract were then washed twice with 1 M citric acid, once with brine, twice with saturated aq sodium bicarbonate, and again with brine. The organic phase was then dried with MgSO4, filtered and concentrated in vacuo. The solid was suspended in diethyl ether, sonicated and filtered to give a second crop of the title compound as a white solid (5.79 g, 19%).

후처리

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane (500 mL)
  3. customthe solvents were removed in vacuo
  4. stirringthe residue was stirred vigorously with ethyl acetate and water for several hours
  5. filtrationThe mixture was filtered
  6. customto give a white solid, which
  7. washwas washed with ethyl acetate
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-30f7bf1acb894d45adf7f91c0e0b1e69
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700628B2

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