Benzoic acid, 2-chloro-5-(chlorosulfonyl)- → h-NTPDase8-IN-1

HRID 59301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 59301
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:15]1([NH2:18])[CH2:17][CH2:16]1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](=[O:13])(=[O:12])[NH:18][CH:15]2[CH2:17][CH2:16]2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

4

Edukt 2

HCID 67306Benzoic acid, 2-chloro-5-(chlorosulfonyl)-HCID 69828Cyclopropylamine

Produkt 1

HCID 16768315h-NTPDase8-IN-1Ausbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-5-(chlorosulfonyl)benzoic acid (4.0 g, 15.68 mmol) in DCM (60 mL) was added cyclopropyl amine (1.8 g, 31.57 mmol) and the reaction mixture was stirred at RT for 16 h. The reaction mass was concentrated and the residue was diluted with ice cold water and acidified with dilute HCl. The crude solid was filtered off, washed with water and dried to afford 3.0 g of pure product. 1H NMR (300 MHz, DMSO d6): δ 0.37 (s, 2H), 0.49 (d, J=5.4 Hz, 2H), 2.12-2.13 (m, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.91 (d, J=8.4 Hz, 1H), 8.13 (s, 1H), 8.18 (s, 1H), 13.92 (br s, 1H).

Aufarbeitung

  1. concentrationThe reaction mass was concentrated
  2. additionthe residue was diluted with ice cold water
  3. filtrationThe crude solid was filtered off
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-57f2ee6e028a4bac873e0a391adb8b2d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439890B2

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