Chloroacetaldehyde → N-(3-(thiazol-2-ylamino)phenyl)methanesulfonamide

HRID 1035831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1035831
[NH:1]([C:5]1[CH:6]=[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=1)[C:2]([NH2:4])=[S:3].Cl[CH2:17][CH:18]=O>C(O)C>[S:3]1[CH:18]=[CH:17][N:4]=[C:2]1[NH:1][C:5]1[CH:6]=[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=1

Komponenten

4

Edukt 2

HCID 33ChloroacetaldehydeHCID 86674185N-(3-thioureidophenyl)methanesulfonamide

Produkt 1

HCID 86674184N-(3-(thiazol-2-ylamino)phenyl)methanesulfonamideAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N-(3-thioureidophenyl)methanesulfonamide 54 (1.14 g, 4.65 mmol) and 50% aq. chloroacetaldehyde solution (3.65 mL, 23.25 mmol) were taken into ethanol and refluxed for 2 hours. Reaction mixture was concentrated and aq. Saturated NaHCO3 was added. Resulting light brown solid was filtered and washed with water, dried under high vacuum to obtain N-(3-(thiazol-2-ylamino)phenyl)methanesulfonamide 55 (1.17 g, 93% yield). Resulting product was further used without further purification. MS (ES) m/z 270 (M+H+).

Aufarbeitung

  1. temperaturerefluxed for 2 hours
  2. customReaction mixture
  3. concentrationwas concentrated
  4. additionaq. Saturated NaHCO3 was added
  5. customResulting light brown solid
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-decce2a17b204d4fa75e7d5ccb75194b
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546400B2

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