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

HRID 40311

Reaction equation

HRID 40311 reaction equation
C(N(CC)C(C)C)(C)C.Br[C:11]1[S:12][CH:13]=[C:14]([Br:16])[N:15]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>CCO>[Br:16][C:14]1[N:15]=[C:11]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[S:12][CH:13]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 27632972,4-Dibromo-1,3-thiazole

Product 1

HCID 438110424-(4-Bromo-1,3-thiazol-2-yl)morpholineYield 68.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

To a microwave vial was added N,N-diisopropylethylamine (0.86 ml, 4.9 mmol), 2,4-dibromothiazole (1.00 g, 4.1 mmol), and morpholine (0.43 ml, 4.9 mmol) in EtOH (4 mL). The mixture was heated under microwave irradiation at 140° C. for 35 minutes. The reaction mixture was concentrated in vacuo. The crude material was dissolved in minimal DCM/MeOH and purified via MPLC (eluting with 0-30% EtOAc in hexanes) to yield 4-(4-bromothiazol-2-yl)morpholine (0.700 g, 68% yield) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe crude material was dissolved in minimal DCM/MeOH
  3. custompurified via MPLC (eluting with 0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f5d6627eee1f4de1a5d7c92be3874165
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Linked notes

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