Water → 1-isobutyl-1H-thieno[2,3-d][1,3]oxazine-2,4-dione

HRID 1724659

Reaktionsgleichung

Reaktionsgleichung von HRID 1724659
[CH2:1]([NH:5][C:6]1[S:7][CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[CH:2]([CH3:4])[CH3:3].[OH-].[Na+].O.ClC(Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl.CO>[CH2:1]([N:5]1[C:6]2[S:7][CH:8]=[CH:9][C:10]=2[C:11](=[O:12])[O:13][C:14]1=[O:21])[CH:2]([CH3:4])[CH3:3]

Komponenten

7

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 94429TriphosgeneHCID 67317044Methyl 2-(isobutylamino)thiophene-3-carboxylate

Produkt 1

HCID 866016361-isobutyl-1H-thieno[2,3-d][1,3]oxazine-2,4-dioneAusbeute 89,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-(isobutylamino)thiophene-3-carboxylate (2.1 g, 9.9 mmol), sodium hydroxide (0.39 g, 9.8 mmol), water (20 mL) and methanol (10 mL) was heated at reflux for 2 h and cooled to room temperature. Methanol was removed under reduced pressure; the residue was diluted with dichloromethane (10 mL) and cooled to 0° C. Triphosgene (5.85 g, 19.7 mmol) was added portionwise; the reaction mixture was stirred for 18 h and diluted with dichloromethane. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to provide the crude product as a light brown solid (2.0 g). This material was used in the next step (Step D) without any purification. 1H NMR (400 MHz, CDCl3): δ 7.25 (d, 1 H), 6.95 (d, 1 H), 3.79 (d, 2 H), 2.40-2.36 (m, 1 H), 1.02 (d, 6 H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customMethanol was removed under reduced pressure
  4. additionthe residue was diluted with dichloromethane (10 mL)
  5. temperaturecooled to 0° C
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9e91cb72c15748fca301e30afa21a454
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07488736B2

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