Hydrochloric Acid → 3-Methylsulfonyl-4-trifluoromethoxyphenyl isocyanate

HRID 1633941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633941
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][C:11]=1[O:12][C:13]([F:16])([F:15])[F:14])[NH2:8])(=[O:4])=[O:3].Cl.C1(C)C=CC=CC=1.Cl[C:26](OC(Cl)(Cl)Cl)=[O:27]>C(OCC)(=O)C>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([N:8]=[C:26]=[O:27])[CH:9]=[CH:10][C:11]=1[O:12][C:13]([F:14])([F:15])[F:16])(=[O:4])=[O:3]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 10426Diphosgene2×HCID 223111603-Methylsulfonyl-4-trifluoromethoxyaniline

Produkt 1

HCID 223111583-Methylsulfonyl-4-trifluoromethoxyphenyl isocyanate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To 3-methylsulfonyl-4-trifluoromethoxyaniline (2.0 mmol, 500 mg) dissolved in ethyl acetate (6 ml) was added 3N HCl in ethyl acetate (5 ml) followed by concentration in vacuo. The residue was treated with toluene (3×5 mL) and each time concentrated in vacuo. To the residue was added toluene (10 mL) and trichloromethyl chloroformate (6 mmol, 0.73 mL), and under a N2atmosphere the suspension was gently refluxed for 2 hours at 120° C. Additional trichloromethyl chloroformate (6 mmol, 0.73 mL) was added and refluxing was continued overnight. The reaction mixture was concentrated in vacuo to afford 3-methylsulfonyl-4-trifluoromethoxyphenyl isocyanate.

Aufarbeitung

  1. concentrationfollowed by concentration in vacuo
  2. additionThe residue was treated with toluene (3×5 mL)
  3. concentrationeach time concentrated in vacuo
  4. temperaturerefluxing
  5. concentrationThe reaction mixture was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-887f0d6e9d934277bfd9f6c8950f75a4
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503949B1

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