Diethanolamine → 2-Bis(2-hydroxyethyl)amino-5-nitrobenzonitrile

HRID 1744525ノート

反応式

HRID 1744525 の反応式
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[NH:13]([CH2:17][CH2:18][OH:19])[CH2:14][CH2:15][OH:16]>[N+]([O-])([O-])=O.[Ag+]>[OH:16][CH2:15][CH2:14][N:13]([CH2:17][CH2:18][OH:19])[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5]

参加物

4

反応物 2

HCID 8113DiethanolamineHCID 855042-Chloro-5-nitrobenzonitrile

生成物 1

HCID 77213002-Bis(2-hydroxyethyl)amino-5-nitrobenzonitrile収率 60.4%

試薬・触媒・溶媒 1

HCID 24470Silver Nitrate触媒

反応条件

温度
100 °C

実験手順

2-Chloro-5-nitrobenzonitrile (25.5 g) and silver nitrate (28.5 g) were added to diethanolamine (102 g) and the mixture was stirred at 100° C. for 1 h. The reaction mixture was cooled to room temperature and the solid was filtered off. To the filtrate was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from hydrous methanol to give 2-bis(2-hydroxyethyl)amino-5-nitrobenzonitrile (21.2 g).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe solid was filtered off
  3. additionTo the filtrate was added water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customafter which the solvent was evaporated under reduced pressure
  8. additionDiisopropyl ether was added to the residue
  9. customcrystallization
  10. customThe crystals were recrystallized from hydrous methanol

出典と根拠

ORDレコード
ord-150f4cab4bcf4205af37c08d687579e8
出典データセット
uspto-grants-2006_03
特許番号
US07015218B1

反応ノート

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