1-Bromo-4-(chloro(isocyanato)methyl)benzene → HCID 86732297, Verbindung

HRID 517176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517176
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Cl)[N:9]=[C:10]=[O:11])=[CH:4][CH:3]=1.[CH3:13][C:14]1([CH3:32])[C:19](=[O:20])[CH:18]=[C:17]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH2:16][CH2:15]1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:18]3[C:19](=[O:20])[C:14]([CH3:32])([CH3:13])[CH2:15][CH2:16][C:17]=3[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:30])[F:31])[CH:23]=3)[C:10](=[O:11])[NH:9]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 116874181-Bromo-4-(chloro(isocyanato)methyl)benzene2×HCID 867322966,6-Dimethyl-3-(3-(trifluoromethyl)phenylamino)cyclohex-2-enone2×

Produkt 1

HCID 86732297HCID 86732297, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 1-bromo-4-(chloro(isocyanato)methyl)benzene (569 mg, 2.31 mmol) in dichloromethane (5 mL) is added to a solution of 6,6-dimethyl-3-(3-(trifluoromethyl)-phenylamino)cyclohex-2-enone (intermediate 6, 654 mg, 2.31 mmol) in dichloromethane (15 mL), and the resulting mixture is heated at reflux for 4 h and stirred at room temperature over night. Another portion of 1-bromo-4-(chloro(isocyanato)methyl)benzene (283 mg, 1.15 mmol) is added and the mixture is heated at reflux for 24 h. The mixture is cooled to room temperature and all volatiles are evaporated. The residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 90:10 to 60:40). Yield: 372 mg; ESI mass spectrum: [(79Br)-M+H]+=493, [(81Br)-M+H]+=495; Retention time HPLC: 1.37 min (Z005—001).

Aufarbeitung

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 4 h
  3. temperaturethe mixture is heated
  4. temperatureat reflux for 24 h
  5. temperatureThe mixture is cooled to room temperature
  6. customall volatiles are evaporated
  7. customThe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 90:10 to 60:40)
  8. custom1.37 min (Z005—001)

Quellen und Nachweise

ORD-Eintrag
ord-9332af675c264582a9133f172a674dd3
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115093B2

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