Benzene → Bromobutide

HRID 1577469

Reaktionsgleichung

Reaktionsgleichung von HRID 1577469
[Br:1][CH:2]([C:6]([CH3:9])([CH3:8])[CH3:7])[C:3](O)=[O:4].C1C=CC=CC=1.[CH3:16][C:17]([NH2:25])([CH3:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[CH3:16][C:17]([NH:25][C:3](=[O:4])[CH:2]([C:6]([CH3:9])([CH3:8])[CH3:7])[Br:1])([CH3:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 241BenzeneHCID 10868DicyclohexylcarbodiimideHCID 68509CumylamineHCID 1842512-Bromo-3,3-dimethylbutanoic Acid

Produkt 1

HCID 53079BromobutideAusbeute 68,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Into a 200 ml four-necked flask, there were charged α-bromo-tert-butylacetic acid (9.8 g) and benzene (50 ml), and pyridine (50 ml) and α,α-dimethylbenzylamine (6.9 g) were dropwise added thereto while stirring at room temperature. Dicyclohexylcarbodiimide (10.8 g) was further added thereto, and the reaction was continued at 60°-70° C. for 6 hours, followed by cooling. The solvent was distilled off under reduced pressure, and the residue was extracted with hot benzene. The benzene extract was concentrated by distillation, and the residue was recrystallized from ethanol to give N-(α,α-dimethylbenzyl)-α-bromo-tert-butylacetamide (10.8 g).

Aufarbeitung

  1. additionwere dropwise added
  2. temperatureby cooling
  3. distillationThe solvent was distilled off under reduced pressure
  4. extractionthe residue was extracted with hot benzene
  5. extractionThe benzene extract
  6. concentrationwas concentrated by distillation
  7. customthe residue was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-f5fd1af2f93548e8849b7c91813b75d6
Quelldatensatz
uspto-grants-1981_09
Patentnummer
US04288244

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