Dimethylsulphamoyl chloride → N,N-dimethyl-N'-(2-oxo-2,3-dihydro-1H-indol-5-yl)sulfamide

HRID 1615202

Reaktionsgleichung

Reaktionsgleichung von HRID 1615202
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[CH3:12][N:13]([CH3:18])[S:14](Cl)(=[O:16])=[O:15]>C(OCC)(=O)C.CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:12][N:13]([CH3:18])[S:14]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2)(=[O:16])=[O:15]

Komponenten

5

Edukt 2

HCID 83372Dimethylsulphamoyl chlorideHCID 27732135-Amino-2-oxindole

Produkt 1

HCID 69812379N,N-dimethyl-N'-(2-oxo-2,3-dihydro-1H-indol-5-yl)sulfamideAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 22989253N,N-dimethylformamide ethyl acetateLösungsmittel

Versuchsvorschrift

To 5-aminoindolin-2-one (100 mg, 0.68 mmol) in ethyl acetate/DMF 1:1 (2 mL) was added dimethylsulfamoyl chloride (290 mg, 2.04 mmol) and DMAP (1 mg). After 72 h the product was precipitated with ether, filtered and dried to give 56 mg, 32% of a white solid. 1H NMR (400 MHz, CD3OD) δ 7.21 (s, 1H), 7.16 (d, J=7.0 Hz, 1H), 7.00 (d, J=8.0 Hz, 1H), 3.53 (s, 2H), 2.77 (s, 6H).

Aufarbeitung

  1. customAfter 72 h the product was precipitated with ether
  2. filtrationfiltered
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9de4efba5023491ca359db0caef9324f
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765748B2

Verknüpfte Notizen

Wird geladen…