Hydrochloric Acid → 1-(6,7-Dichloro-2,3-dimethoxyquinoxalin-5-yl)-3-hydroxypropyl methyl sulphone

HRID 1458565

Reaktionsgleichung

Reaktionsgleichung von HRID 1458565
[O:1]=[O+][O-].[CH3:4][S:5]([CH:8]([C:12]1[C:21]([Cl:22])=[C:20]([Cl:23])[CH:19]=[C:18]2[C:13]=1[N:14]=[C:15]([O:26][CH3:27])[C:16]([O:24][CH3:25])=[N:17]2)[CH2:9][CH:10]=C)(=[O:7])=[O:6].[BH4-].[Na+].Cl>ClCCl>[CH3:4][S:5]([CH:8]([C:12]1[C:21]([Cl:22])=[C:20]([Cl:23])[CH:19]=[C:18]2[C:13]=1[N:14]=[C:15]([O:26][CH3:27])[C:16]([O:24][CH3:25])=[N:17]2)[CH2:9][CH2:10][OH:1])(=[O:7])=[O:6]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 220970431-(6,7-Dichloro-2,3-dimethoxyquinoxalin-5-yl)-3-butenyl methyl sulphone

Produkt 1

HCID 220970511-(6,7-Dichloro-2,3-dimethoxyquinoxalin-5-yl)-3-hydroxypropyl methyl sulphoneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ozone was bubbled through a solution of 1-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-3-butenyl methyl sulphone (50 mg, 0.128 mmol) [Example 93(a)] in dry dichloromethane (1.3 ml) at -78° C. until a blue colour developed. The mixture was stirred for 5 minutes and was then purged with a stream of oxygen and then nitrogen. Methanol (1.3 ml) was added and the mixture allowed to equilibrate at -78° C. before sodium borohydride (12 mg, 0.319 mmol) was added in two portions. The mixture was stirred for 5 mins and was then allowed to warm to room temperature. The mixture was poured into 2M hydrochloric acid (20 ml) and extracted with dichloromethane (2×20 ml). The combined extracts were washed with brine (20 ml), dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with 1:1 hexane:ethyl acetate) to give 1-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-3-hydroxypropyl methyl sulphone (35.6 mg, 70%) as a white foam.

Aufarbeitung

  1. customwas then purged with a stream of oxygen
  2. additionMethanol (1.3 ml) was added
  3. additionwas added in two portions
  4. stirringThe mixture was stirred for 5 mins
  5. extractionextracted with dichloromethane (2×20 ml)
  6. washThe combined extracts were washed with brine (20 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (eluting with 1:1 hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c38b5c26c5d94cf99997e8c14f2f8eb2
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852016

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