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

HRID 340658

反応式

HRID 340658 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e98c02bf78c5443a92616f03a336d994
出典データセット
uspto-grants-2014_11
特許番号
US08895599B2

関連ノート

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