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

HRID 1744525

반응식

HRID 1744525 반응식
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]

참가 물질

4

반응물 2

HCID 8113DiethanolamineHCID 855042-Chloro-5-nitrobenzonitrile

생성물 1

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

시약·촉매·용매 1

HCID 24470Silver Nitrate촉매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-150f4cab4bcf4205af37c08d687579e8
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015218B1

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