P-Toluenesulfonamide → 5-Chloro-2-tosylisoindoline

HRID 41400

Reaktionsgleichung

Reaktionsgleichung von HRID 41400
[H-].[Na+].[C:3]1([CH3:13])[CH:8]=[CH:7][C:6]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[CH2:23]Br>CN(C=O)C>[Cl:22][C:19]1[CH:18]=[C:17]2[C:16](=[CH:21][CH:20]=1)[CH2:15][N:12]([S:9]([C:6]1[CH:5]=[CH:4][C:3]([CH3:13])=[CH:8][CH:7]=1)(=[O:10])=[O:11])[CH2:23]2

Komponenten

5

Edukt 3

HCID 6269P-ToluenesulfonamideHCID 24758Sodium hydrideHCID 150082261,2-Bis(bromomethyl)-4-chlorobenzene

Produkt 1

HCID 151678915-Chloro-2-tosylisoindolineAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a suspension of 60% sodium hydride (3.0 g, 0.125 mmol) in mineral oil in 80 ml of anhydrous DMF (100 ml) was dropwise added a solution of para-toluene sulphonamide (5.6 g, 32.60 mmol) in 30 ml of DMF over 1 hour with vigorous stirring at room temperature. After the addition, the mixture was stirred for 1 hour at room temperature and another 1 hour heating at 90° C. To this mixture was added dropwise a solution of 1,2-bis-bromomethyl-4-chloro-benzene (4 g, 14.18 mmol) in 20 ml of anhydrous DMF at 60° C. and then stirred overnight at room temperature. The resultant mixture was poured onto ice and the resulting precipitate was collected by filtration. The precipitate was washed with 1N hydrochloric acid, 5% sodium carbonate and brine then dried (MgSO4), filtered and evaporated to give 2.8 g of 5-Chloro-2-(toluene-4-sulphonyl)-2,3-dihydro-1H-isoindole as a pale yellow solid. MS: [M+H]+ 308

Aufarbeitung

  1. additionAfter the addition
  2. stirringthe mixture was stirred for 1 hour at room temperature and another 1 hour
  3. temperatureheating at 90° C
  4. stirringstirred overnight at room temperature
  5. filtrationthe resulting precipitate was collected by filtration
  6. washThe precipitate was washed with 1N hydrochloric acid, 5% sodium carbonate and brine
  7. dry with materialthen dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-e46a8b15d74247f19833f1cb90d740fc
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530469B2

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