Morpholine → 4-(4-Chlorothiazol-2-YL)morpholine

HRID 1432732Notes

Reaction equation

HRID 1432732 reaction equation
Cl[C:2]1[S:3][CH:4]=[C:5]([Cl:7])[N:6]=1.[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[Cl:7][C:5]1[N:6]=[C:2]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[S:3][CH:4]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 123331552,4-Dichlorothiazole

Product 1

HCID 534400954-(4-Chlorothiazol-2-YL)morpholineYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

In a 75 mL dry pressure vessel, 2,4-dichloro-thiazole (500 mg, 3.2 mmol) and morpholine (560 μL, 6.4 mmol) are dissolved in dry THF (2.0 mL). Cs2CO3 (1.56 g, 4.8 mmol) is added, and the reaction vessel is sealed. The reaction mixture is heated to 110° C. overnight. Solvent is removed via reduced pressure, and the crude reaction mixture is purified via silica gel chromatography to give the title compound (597 mg, 2.92 mmol, 91%). 1H-NMR (CDCl3), δ 3.45 (m, 4H), 3.79 (m, 4H), 6.31 (s, 1H) ppm. ES-MS (m/z): calcd for C7H9ClN2OS (M+H)+: 204.68; found: 205.2.

Workup

  1. customIn a 75 mL dry pressure vessel
  2. customthe reaction vessel is sealed
  3. customSolvent is removed via reduced pressure
  4. customthe crude reaction mixture
  5. customis purified via silica gel chromatography

Sources & evidence

ORD record
ord-020b1cf2dd0c47dea9e2640f080cfca6
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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