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Triethylamine → 4-Methanesulfonyl-6-methyl-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 1295557
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1295557
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:11]=1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([N:7]1[C:6]2[CH:11]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[O:10][CH2:9][CH2:8]1)(=[O:22])=[O:21]
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6494096-methyl-3,4-dihydro-2H-1,4-benzoxazine

Produkt 1

HCID 694178614-Methanesulfonyl-6-methyl-3,4-dihydro-2H-benzo[1,4]oxazineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

6-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine (1.49 g, 10 mmol) was dissolved in dichloromethane (50 mL) and treated with triethylamine (1.14 g, 11 mmol) followed by the dropwise addition of methanesulfonyl chloride (1.26 g, 11 mmol). The mixture was stirred at ambient temperature for 18 h then evaporated to dryness under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous NaHCO3. The phases were separated and the organic phase washed with water, saturated brine, dried (MgSO4) and evaporated to dryness under reduced pressure to give the title compound (2.09 g, 93%) as a brown solid.

Aufarbeitung

  1. customthen evaporated to dryness under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous NaHCO3
  3. customThe phases were separated
  4. washthe organic phase washed with water, saturated brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-028e2a324f354eb7aea644437ba0f178
Quelldatensatz
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07244726B2

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