Morpholine → 4-(1,3-Thiazol-2-yl)morpholine

HRID 244485Notes

Reaction equation

HRID 244485 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>O>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 764302-Bromothiazole

Product 1

HCID 154758374-(1,3-Thiazol-2-yl)morpholineYield 75.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-bromothiazole (356 μL, 4.00 mmol) in morpholine (2.09 mL, 24.0 mmol) was warmed at 100° C. in a sealed tube. After 61 hours, the mixture was cooled to room temperature, diluted with 20 mL of water, and extracted with three 30 mL portions of diethyl ether. The combined organic layers were washed with five 30 mL portions of water, 30 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed over SiO2 (20-100% ethyl acetate in hexanes, gradient) to afford 513 mg (75%) of 4-thiazol-2-yl-morpholine.

Workup

  1. extractionextracted with three 30 mL portions of diethyl ether
  2. washThe combined organic layers were washed with five 30 mL portions of water, 30 mL of brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed over SiO2 (20-100% ethyl acetate in hexanes, gradient)

Sources & evidence

ORD record
ord-5e6803b3a4184742bdd816b014b0bbdb
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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