2-Aminobenzaldehyde → 2-(2,6-dichloro-3-nitro-phenyl)-N-(2-formyl-phenyl)-acetamide

HRID 270698

반응식

HRID 270698 반응식
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]([OH:15])=O.[NH2:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[O:20]>S(Cl)(Cl)=O.ClCCl.CCOC(C)=O>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]([NH:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[O:20])=[O:15]

참가 물질

6

반응물 2

HCID 682552-AminobenzaldehydeHCID 542654372,6-Dichloro-3-nitrophenylacetic acid

생성물 1

HCID 598338822-(2,6-dichloro-3-nitro-phenyl)-N-(2-formyl-phenyl)-acetamide수율 88.6%

시약·촉매·용매 3

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매HCID 24386Thionyl Chloride용매

실험 절차

A solution of (2,6-dichloro-3-nitro-phenyl)-acetic acid (0.90 g, 3.35 mmol) in thionyl chloride (15 mL) is refluxed for one hour. The solvent is removed by concentration and dry toluene is added to thoroughly remove thionyl chloride. To the solution of acid chloride in dry dichloromethane (30 mL) is added (drop-wise) a solution of 2-aminobenzaldehyde (0.365 g, 3.02 mmol) in dichloromethane (5.0 mL). The mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with EtOAc and washed with saturated K2CO3 and brine. The organic layer is dried, filtered and concentrated to give crude product (0.94 g, 88.6%).

후처리

  1. customThe solvent is removed by concentration and dry toluene
  2. additionis added to thoroughly remove thionyl chloride
  3. washwashed with saturated K2CO3 and brine
  4. customThe organic layer is dried
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-85921cc9266e4e75939cb8df0dbc30ea
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449582B2

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