Sulfuryl chloride → 9-chlorosulfonyl-5,6-dihydro-5-oxo-11H-indeno[1,2-c] Isoquinoline

HRID 2306568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2306568
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2[CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:4]=2[NH:3]1.[Cl:19][S:20](Cl)(=[O:22])=[O:21]>>[Cl:19][S:20]([C:15]1[CH:16]=[CH:17][C:18]2[C:4]3[NH:3][C:2](=[O:1])[C:11]4[C:6]([C:5]=3[CH2:12][C:13]=2[CH:14]=1)=[CH:7][CH:8]=[CH:9][CH:10]=4)(=[O:22])=[O:21]

Komponenten

3

Edukt 2

HCID 24648Sulfuryl chlorideHCID 101053885,6-dihydro-5-oxo-11H-indeno [1,2-c]isoquinoline

Produkt 1

HCID 112328219-chlorosulfonyl-5,6-dihydro-5-oxo-11H-indeno[1,2-c] IsoquinolineAusbeute 92,2 %

Versuchsvorschrift

Compound 6 (40 g, 0.17 mol) was added in small portions to chlorosulfonyl chloride (112 mL, 1.71 mol) at 0°C. and the reaction mixture was allowed to warm to room temperature and stir for 2 h. The reaction mixture was slowly poured on ice and the resulting yellow solid was filtered, washed thoroughly with water and EtOAc and dried in vacuo to provide the above-titled product 7 (52 g, 92%). 1H NMR (DMSO-D6): δ 3.91 (s, 2H), 7.43-7.48 (m, 1H), 7.60 (d, J=7.2 Hz, 1H), 7.74-7.76 (m, 2H), 7.79 (s, 1H), 7.90 (d, J=7.5 Hz, 1H), 8.23 (d, J=7.8 Hz, 1H), Anal. Calcd for C16H12ClNO4S: C, 54.94; H, 3.46; N, 4.00. Found C, 55.28; H, 3.43, N, 3.68, Karl-Fisher, 2.95.

Aufarbeitung

  1. additionThe reaction mixture was slowly poured on ice
  2. filtrationthe resulting yellow solid was filtered
  3. washwashed thoroughly with water and EtOAc
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d3263d77439b471dbcd1dca5d37d20ff
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06828319B2

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