Triethylamine → 7-Methanesulfonylmethyl-4-chloroquinoline

HRID 965001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 965001
O[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(=O)=O.CC(C)=O.C(OCC)(=O)C>[CH3:21][S:22]([CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([Cl:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1)(=[O:24])=[O:23]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 22054610(4-Chloroquinolin-7-yl)methanol

Produkt 1

HCID 190751107-Methanesulfonylmethyl-4-chloroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 18522661Acetone cardiceLösungsmittel

Versuchsvorschrift

7-Hydroxymethyl-4-chloroquinoline (930 mg, 4.82 mmol) dissolved in anhydrous methylene chloride (40 ml) was added with triethylamine (679 mg, 6.72 mmol). The mixture was cooled in dry ice/acetone bath, added dropwise with methanesulfonyl chloride (770 mg, 6.7 mmol) and the reactant was stirred for 20 minutes without the cooling bath. Then, the reactant was added under ice-water cooling with cool aqueous solution of saturated sodium bicarbonate (40 ml) and ethyl acetate (150 ml) and shaken to separate the organic layer. The separated organic layer was washed with saturated saline solution and dried over magnesium sulfate. The solvent was removed to obtain 7-methanesulfonylmethyl-4-chloroquinoline as oily product.

Aufarbeitung

  1. stirringshaken
  2. customto separate the organic layer
  3. washThe separated organic layer was washed with saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-dd8a4311f2744953aaa33480d6579f42
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773449

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