Water → HCID 23336373, Verbindung

HRID 903554

Reaktionsgleichung

Reaktionsgleichung von HRID 903554
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([Cl:21])[C:18]=1[O:19][CH3:20])[NH2:15])=[O:11].C(N(CC)[C:25](Cl)=[S:26])C.ClC1C=CC=CC=1.O>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([C:12]1[CH:13]=[C:14]([N:15]=[C:25]=[S:26])[CH:16]=[C:17]([Cl:21])[C:18]=1[O:19][CH3:20])=[O:11]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7964ChlorobenzeneHCID 66607Diethylthiocarbamoyl chlorideHCID 233363743-[N-(2,6-dimethylphenyl)carbamoyl]-4-methoxy-5-chloroaniline

Produkt 1

HCID 23336373HCID 23336373, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-[N-(2,6-dimethylphenyl)carbamoyl]-4-methoxy-5-chloroaniline (650 mg), diethylthiocarbamoyl chloride (360 mg) and chlorobenzene (6 ml) is refluxed for 30 minutes. The reaction mixture is mixed with water and shaken with methylene chloride. The organic layer is washed with water, dried over Glauber's salt and concentrated to remove the solvent. The residue is chromatographed on a column of silica gel, which is eluted with methylene chloride. The eluted fractions are collected and the solvent is evaporated. The residue is recrystallized from ethyl acetate to give 3-[N-(2,6-dimethylphenyl)carbamoyl]-4-methoxy-5-chlorophenyl isothiocyanate (340 mg) as crystals melting at 191°-192.5° C.

Aufarbeitung

  1. temperatureis refluxed for 30 minutes
  2. washThe organic layer is washed with water
  3. dry with materialdried over Glauber's salt
  4. concentrationconcentrated
  5. customto remove the solvent
  6. customThe residue is chromatographed on a column of silica gel, which
  7. washis eluted with methylene chloride
  8. customThe eluted fractions are collected
  9. customthe solvent is evaporated
  10. customThe residue is recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a3e6b58fc0954193b9c017c69ae5ecdc
Quelldatensatz
uspto-grants-1980_10
Patentnummer
US04228165

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