Dimethylformamide → N-(2-nitrophenyl)-4-benzyloxy-3-methoxybenzamide

HRID 340658

반응식

HRID 340658 반응식
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.S(Cl)(Cl)=O.[N+:29]([C:32]1[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=1[NH2:34])([O-:31])=[O:30]>C(Cl)Cl.O.N1C=CC=CC=1>[N+:29]([C:32]1[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=1[NH:34][C:13](=[O:15])[C:12]1[CH:16]=[CH:17][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([O:18][CH3:19])[CH:11]=1)([O-:31])=[O:30]

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 69462-NitroanilineHCID 24386Thionyl ChlorideHCID 2263354-(Benzyloxy)-3-methoxybenzoic acid

생성물 1

HCID 66911323N-(2-nitrophenyl)-4-benzyloxy-3-methoxybenzamide수율 51.5%

시약·촉매·용매 3

HCID 962Water용매HCID 1049Pyridine용매HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

In 20 ml of methylene chloride was suspended 2.0 g (7.7 mmol) of 4-benzyloxy-3-methoxy benzoic acid. DMF (0.05 g) and thionyl chloride (0.68 ml) were added to this suspension. The mixture was stirred at 50° C. for 2 hours. At a temperature of 0° C., 20 ml of pyridine wherein 1.1 g (8.0 mmol) of 2-nitroaniline had been dissolved at room temperature was added dropwise to the mixture. The mixture was stirred for 2 hours at room temperature, and water was added thereto to extract the methylene chloride phase. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The crystals thus obtained were recrystallized using methylene chloride-hexane, thereby yielding 1.5 g of N-(2-nitrophenyl)-4-benzyloxy-3-methoxybenzamide crystals.

후처리

  1. additionwas added dropwise to the mixture
  2. stirringThe mixture was stirred for 2 hours at room temperature
  3. extractionto extract the methylene chloride phase
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe crystals thus obtained
  7. customwere recrystallized

출처 및 근거

ORD 기록
ord-e98c02bf78c5443a92616f03a336d994
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895599B2

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