Morpholine → 4-(Morpholin-4-ylmethyl)-1,3-thiazol-2-amine

HRID 1684947

Reaktionsgleichung

Reaktionsgleichung von HRID 1684947
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl.Cl[CH2:9][C:10]1[N:11]=[C:12]([NH2:15])[S:13][CH:14]=1>CN(C=O)C.C(OCC)(=O)C>[O:4]1[CH2:5][CH2:6][N:1]([CH2:9][C:10]2[N:11]=[C:12]([NH2:15])[S:13][CH:14]=2)[CH2:2][CH2:3]1

Komponenten

5

Edukt 2

HCID 8083MorpholineHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)

Produkt 1

HCID 21253444-(Morpholin-4-ylmethyl)-1,3-thiazol-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Morpholine (350 μL, 4.0.0 mmol) is added to a solution of 4-chloromethyl-thiazol-2-ylamine hydrochloride (368 mg, 2.00 mmol) in DMF (7 mL). The reaction is stirred at 90° C. for 16 h. The reaction is diluted with ethyl acetate and washed with water. The aqueous layer is concentrated in vacuo and extracted with ethyl acetate. The combined organic layers are dried over MgSO4 and evaporated to give brown crystals which are used without further purification. 1H-NMR (400 MHz, d6-DMSO) δ=2.41-2.42 (m, 4H, CH2CH2), 3.30 (s, 2H, CH2), 3.55-3.60 (m, 4H, CH2CH2), 6.33 (s, 1H, Har), 6.85 (bs, 2H, NH2).

Aufarbeitung

  1. washwashed with water
  2. concentrationThe aqueous layer is concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. customevaporated
  6. customto give brown crystals which
  7. customare used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-f5185dbf08d14591b0c720c939f657fc
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148369B2

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