Dimethylcarbamoyl Chloride → Tert-butyl (2-(3,3-dimethylureido)-4-(thiophen-2-yl)phenyl)carbamate

HRID 62697

Reaktionsgleichung

Reaktionsgleichung von HRID 62697
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>N1C=CC=CC=1.C1(C)C=CC=CC=1.O>[CH3:21][N:22]([CH3:26])[C:23](=[O:24])[NH:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18]

Komponenten

6

Edukt 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

Produkt 1

HCID 71007375Tert-butyl (2-(3,3-dimethylureido)-4-(thiophen-2-yl)phenyl)carbamateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-amino-4-(thiophen-2yl)phenylcarbamate (0.12 g, 0.41 mmol, 1.0 equiv.) in pyridine (2 mL) was added a solution of dimethylcarbamic chloride (0.07 g, 0.62 mmol, 1.5 equiv.) in toluene (0.3 mL). The resulting solution was stirred at room temperature overnight. The crude residue was diluted with water (10 mL) and extracted with ethyl acetate (10 mL×2). The combined organic layers were washed with water (10 mL), dried, filtered and concentrated. The crude residue was washed with petroleum ether (5 mL) to afford tert-butyl (2-(3,3-dimethylureido)-4-(thiophen-2-yl)phenyl)carbamate (0.12 g, 80% yield).

Aufarbeitung

  1. extractionextracted with ethyl acetate (10 mL×2)
  2. washThe combined organic layers were washed with water (10 mL)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe crude residue was washed with petroleum ether (5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-5aa9c5dd39104fa98b5ad0aa30f21e19
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447030B2

Verknüpfte Notizen

Wird geladen…