Benzenamine, 3,5-bis(trifluoromethyl)- → Phenyl [3,5-bis(trifluoromethyl)phenyl]carbamate

HRID 1633906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633906
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].C(N(CC)C(C)C)(C)C.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27]>ClCCl>[C:29]1([O:28][C:26](=[O:27])[NH:6][C:5]2[CH:4]=[C:3]([C:2]([F:14])([F:15])[F:1])[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

5

Edukt 3

HCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 15891Phenyl chloroformateHCID 81531Diisopropylethylamine

Produkt 1

HCID 16100340Phenyl [3,5-bis(trifluoromethyl)phenyl]carbamateAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3,5-Bis-(trifluoromethyl)aniline (2.0 g, 8.7 mmol) was dissolved in dichloromethane (80 mL) and N,N-diisopropylethylamine (1.6 mL, 9.6 mmol) was added followed by slow addition of phenyl chloroformate (1.1 mL, 8.7 mmol). The resulting mixture was stirred at room temperature for 16 hours. The mixture was successively washed with 1N hydrochloric acid (3×100 mL), water (3×100 mL), a mixture of water and saturated aqueous sodium hydrogen carbonate (1:1, 2×100 mL) and a mixture of water and saturated aqueous sodium chloride (1:1, 3×100 mL), dried (MgSO4) and concentrated in vacuo. The residue was crystallised from heptane containing a little diethyl ether to afford 1.3 g (43%) of (3,5-bis-trifluoromethylphenyl)carbamic acid phenyl ester as a solid.

Aufarbeitung

  1. washThe mixture was successively washed with 1N hydrochloric acid (3×100 mL), water (3×100 mL)
  2. additiona mixture of water and saturated aqueous sodium hydrogen carbonate (1:1, 2×100 mL)
  3. additiona mixture of water and saturated aqueous sodium chloride (1:1, 3×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallised from heptane containing a little diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-66ae1d6ffe444e1d9824c37a2af30a7a
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503949B1

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