5,5-Dimethyl-3-{[3-(trifluoromethyl)phenyl]amino}cyclohex-2-en-1-one → 4-(4-Bromophenyl)-7,7-dimethyl-1-(3-(trifluoromethyl)phenyl)-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione

HRID 517178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517178
[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])[CH2:19][C:18](=[O:20])[CH:17]=[C:16]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH2:15]1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:18](=[O:20])[CH2:19][C:14]([CH3:32])([CH3:13])[CH2:15][C:16]=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 6147225,5-Dimethyl-3-{[3-(trifluoromethyl)phenyl]amino}cyclohex-2-en-1-one2×HCID 116874181-Bromo-4-(chloro(isocyanato)methyl)benzene

Produkt 1

HCID 867322984-(4-Bromophenyl)-7,7-dimethyl-1-(3-(trifluoromethyl)phenyl)-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 1-bromo-4-(chloro(isocyanato)methyl)benzene (435 mg, 1.77 mmol) in dichloromethane (5 mL) is added to a solution of 5,5-dimethyl-3-(3-(trifluoromethyl)-phenylamino)cyclohex-2-enone (intermediate 8, 500 mg, 1.77 mmol) in dichloromethane (15 mL) and the mixture is heated at reflux over night. All volatiles are evaporated and the residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 90:10 to 60:40). Yield: 389 mg; ESI mass spectrum: [(79Br)-M+H]+=493, [(81Br)-M+H]+=495; Retention time HPLC: 1.38 min (Z002—002).

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureat reflux over night
  3. customAll volatiles are evaporated
  4. customthe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 90:10 to 60:40)
  5. custom1.38 min (Z002—002)

Quellen und Nachweise

ORD-Eintrag
ord-329f82c7d1744fc286d56cf83eba67da
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115093B2

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