Hydrochloric Acid → 4-Hexylsulfonamidobenzoylacetonitrile

HRID 344991

Reaktionsgleichung

Reaktionsgleichung von HRID 344991
[CH2:1]([S:7](Cl)(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([CH2:18][C:19]#[N:20])=[O:17])=[CH:14][CH:13]=1.N1C=CC=CC=1.Cl>CO>[CH2:1]([S:7]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([CH2:18][C:19]#[N:20])=[O:17])=[CH:21][CH:22]=1)(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 845041-Hexanesulfonyl chlorideHCID 96920Benzenepropanenitrile, 4-amino-beta-oxo-

Produkt 1

HCID 199934544-HexylsulfonamidobenzoylacetonitrileAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 3.7 grams (0.02 Mol) hexane sulfonyl chloride, 3.2 grams (0.02 Mol) 4-aminobenzoylacetonitrile and 5 mL of pyridine was stirred at 0° C. for 1.5 hours. The resulting very thick brown solution was dissolved in 15 mL of methanol and dropwise added to 100 mL of 2N hydrochloric acid at 0° C. A tan precipitate formed which was stirred for 30 minutes, then filtered and washed with water and dried for 2 hours at 50° C./10 mm Hg to give 6.9 grams of crude product. This was recrystallized from aqueous ethanol to give 4.2 grams (13.6 mMol, 68% yield) of pure product, m.p.=125°-127° C.

Aufarbeitung

  1. customA tan precipitate formed which
  2. filtrationfiltered
  3. washwashed with water
  4. customdried for 2 hours at 50° C./10 mm Hg
  5. customto give 6.9 grams of crude product
  6. customThis was recrystallized from aqueous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-d748453e058a4965bcbe2fd983f4bb90
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05055387

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