O-Methylhydroxylamine hydrochloride → 6-bromo-N-methoxy-1,3,3-trimethyl-2,2-dioxo-pyrido[3,2-c]thiazin-4-imine

HRID 1478539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478539
[CH3:1][O:2][NH2:3].Cl.[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH3:21])[S:11](=[O:20])(=[O:19])[C:12]([CH3:18])([CH3:17])[C:13](=O)[C:14]=2[N:15]=1>N1C=CC=CC=1>[Br:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH3:21])[S:11](=[O:19])(=[O:20])[C:12]([CH3:18])([CH3:17])[C:13](=[N:3][O:2][CH3:1])[C:14]=2[N:15]=1

Komponenten

4

Edukt 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 900436416-Bromo-1,3,3-trimethyl-2,2-dioxo-pyrido[3,2-c]thiazin-4-one

Produkt 1

HCID 1237441886-bromo-N-methoxy-1,3,3-trimethyl-2,2-dioxo-pyrido[3,2-c]thiazin-4-imine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a suspension of MeONH2.HCl (272 mg, 3.26 mmol) in pyridine (5 ml) was added 6-bromo-1,3,3-trimethyl-2,2-dioxo-pyrido[3,2-c]thiazin-4-one (130 mg, 0.41 mmol) and stirring was continued for 2 days at 100° C. The mixture was cooled to ambient temperature then concentrated under reduced pressure followed by addition of water and ethyl acetate then the phases were separated. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography eluting with ethyl acetate/heptane, gradient, afforded 6-bromo-N-methoxy-1,3,3-trimethyl-2,2-dioxo-pyrido[3,2-c]thiazin-4-imine as a yellow solid as a 5/1 mixture of oxime isomers.

Aufarbeitung

  1. concentrationthen concentrated under reduced pressure
  2. additionfollowed by addition of water and ethyl acetate
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography
  9. washeluting with ethyl acetate/heptane, gradient

Quellen und Nachweise

ORD-Eintrag
ord-4487c627a04c4d8ab407b0421d9ae87b
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403845B2

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