Morpholine → HCID 86641320, Verbindung

HRID 1435606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435606
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:7][C:8]1[S:9][C:10]([CH3:18])=[C:11]([CH2:13][C:14](OC)=[O:15])[N:12]=1>C(Cl)Cl>[CH3:18][C:10]1[S:9][C:8]([NH2:7])=[N:12][C:11]=1[CH2:13][C:14]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:15]

Komponenten

4

Edukt 2

HCID 8083MorpholineHCID 2763571Methyl 2-(2-amino-5-methyl-1,3-thiazol-4-yl)acetate

Produkt 1

HCID 86641320HCID 86641320, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of alumiumchloride (0.86 g, 6.44 mmol) in DCM (50 mL) was treated dropwise with morpholine (4.7 mL, 53.7 mmol) giving a colorless solution. Methyl (2-amino-5-methyl-1,3-thiazol-4-yl)acetate (1.0 g, 5.37 mmol) was added (orange solution) and after 1 h, the reaction mixture was quenched with aqueous citric acid (3%, 10 mL) and basified with saturated aqueous sodium bicarbonate. Extraction with DCM (3×50 mL), drying (sodium sulfate) of the combined organic layers and evaporation of the volatiles gave 0.70 g of a yellow foam. Purification of the solid by flash column chromatography on silicagel eluting with DCM/methanol (10/1 v/v) gave 545 mg (42%) of an ivory solid: Anal. Calcd. (found) for C10H15N3O2S: C, 49.7 (49.5)%; H, 6.3 (6.3)%; N, 17.4 (17.3)%; S, 13.3 (13.3).

Aufarbeitung

  1. customgiving a colorless solution
  2. customthe reaction mixture was quenched with aqueous citric acid (3%, 10 mL)
  3. extractionExtraction with DCM (3×50 mL)
  4. customdrying
  5. custom(sodium sulfate) of the combined organic layers and evaporation of the volatiles

Quellen und Nachweise

ORD-Eintrag
ord-64e40c5e48354b5baf0033f45fd67e88
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618961B2

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