Hydrochloric Acid → N-(3,5-Dichlorobenzenesulfonyl)-octahydroisoindole-1-carboxylic acid

HRID 23877

Reaktionsgleichung

Reaktionsgleichung von HRID 23877
[CH:1]1([C:10]([OH:12])=[O:11])[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][NH:2]1.C([O-])([O-])=O.[Na+].[Na+].[Cl:19][C:20]1[CH:21]=[C:22]([S:27](Cl)(=[O:29])=[O:28])[CH:23]=[C:24]([Cl:26])[CH:25]=1.Cl>O>[Cl:26][C:24]1[CH:23]=[C:22]([S:27]([N:2]2[CH2:3][CH:4]3[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5]3)[CH:1]2[C:10]([OH:12])=[O:11])(=[O:28])=[O:29])[CH:21]=[C:20]([Cl:19])[CH:25]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 13207250octahydro-1H-isoindole-1-carboxylic acid

Produkt 1

HCID 22569209N-(3,5-Dichlorobenzenesulfonyl)-octahydroisoindole-1-carboxylic acidAusbeute 192,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Octahydroisoindole-1-carboxylic acid (4.12 gm) was dissolved in a solution of water (125 mL) containing 5.32 g of Na2CO3. Upon complete dissolution, 4.93 g of 3,5-dichlorobenzenesulfonyl chloride was added. The reaction was stirred at rt over night. The reaction mixture was then washed with EtOAc (2×100 mL). The aqueous layer was isolated and acidified to pH=3 by the dropwise addition of a concentrated HCl solution. A solid precipitate formed in the aqueous layer and was filtered and dried in vacuo to afford N-(3,5-dichlorobenzenesulfonyl)-octahydro-isoindole-1-carboxylic acid (14.64 g) as a white solid.

Aufarbeitung

  1. additionwas added
  2. washThe reaction mixture was then washed with EtOAc (2×100 mL)
  3. customThe aqueous layer was isolated
  4. customA solid precipitate formed in the aqueous layer
  5. filtrationwas filtered
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0a2460f200974ace88fcf00015a498c5
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855708B2

Verknüpfte Notizen

Wird geladen…