Toluene → 5-tert.Butylcarbamylphthalid

HRID 1976862

Reaktionsgleichung

Reaktionsgleichung von HRID 1976862
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:9](=[O:10])[O:8][CH2:7]2)([OH:3])=O.CN(C=O)C.C1(C)C=CC=CC=1.[C:26]([NH2:30])([CH3:29])([CH3:28])[CH3:27]>S(Cl)(Cl)=O.C1COCC1>[C:26]([NH:30][C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:9](=[O:10])[O:8][CH2:7]2)=[O:3])([CH3:29])([CH3:28])[CH3:27]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 6385Tert-ButylamineHCID 785171,3-Dihydro-1-oxoisobenzofuran-5-carboxylic acid

Produkt 1

HCID 111489925-tert.Butylcarbamylphthalid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

5-Carboxyphthalid (36 g, 0.2 mole) is suspended in thionylchloride (100 mL). DMF (1.5 mL) is added and the mixture is refluxed for 1 hour. Toluene (200 mL) is added and the solvents are evaporated in vacuo. The residue is dissolved in THF (200 mL) and added to a solution of tert.butylamine (31 g, 0.42 mole) in THF (200 mL) at 5° C. The mixture is allowed to warm to room temperature and stirred overnight. The reaction is then poured into ice water (400 mL) and the precipitated crystals are filtered off. The crystals are washed with water (100 mL). Yield: 41 g, 87%. DSC onset: 189.5° C.

Aufarbeitung

  1. temperaturethe mixture is refluxed for 1 hour
  2. customthe solvents are evaporated in vacuo
  3. dissolutionThe residue is dissolved in THF (200 mL)
  4. filtrationthe precipitated crystals are filtered off
  5. washThe crystals are washed with water (100 mL)
  6. custom189.5° C.

Quellen und Nachweise

ORD-Eintrag
ord-94938be2fcd0455e9ea8ccdb7d16aa64
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06229026B1

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