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

HRID 244486

Reaction equation

HRID 244486 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:7])[N:6]=1.[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1>O>[Br: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

4

Reactant 2

HCID 8083MorpholineHCID 27632972,4-Dibromo-1,3-thiazole

Product 1

HCID 438110424-(4-Bromo-1,3-thiazol-2-yl)morpholineYield 89.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,4-dibromothiazole (500 mg, 2.06 mmol) in morpholine (4.0 mL, 22.3 mmol) was warmed at 50° C. in a sealed tube. After 16 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 was 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 using ethyl acetate in hexanes (0-30% gradient) to afford 458 mg (89%) of 4-(4-bromothiazol-2-yl)morpholine.

Workup

  1. extractionextracted with three 30 mL portions of diethyl ether
  2. washThe combined organic layers was 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

Sources & evidence

ORD record
ord-232160f89dfd47b7a44bd470fa2c75fb
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Linked notes

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