Morpholine → Methyl 2-morpholinothiazole-4-carboxylate

HRID 1424339노트

반응식

HRID 1424339 반응식
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C1COCC1.C(OCC)(=O)C>[O:14]1[CH2:15][CH2:16][N:11]([C:2]2[S:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=2)[CH2:12][CH2:13]1

참가 물질

5

반응물 2

HCID 8083MorpholineHCID 2763213Methyl 2-bromothiazole-4-carboxylate

생성물 1

HCID 86700889Methyl 2-morpholinothiazole-4-carboxylate수율 93.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of methyl 2-bromothiazole-4-carboxylate (0.20 g, 0.901 mmol) in THF (10 mL) was treated with morpholine (0.17 mL, 1.94 mmol) and refluxed for 18 h. The reaction was then diluted with ethyl acetate and washed with sat. NaHCO3 (1×), brine (1×) and dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (2.5×10 cm, 50% AcOEt/CH2Cl2) to give the title material (0.192 g, 92%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ ppm: 7.44 (s, 1H) 3.82 (s, 3H) 3.75 (m, 4H) 3.45 (m, 4H).

후처리

  1. temperaturerefluxed for 18 h
  2. washwashed with sat. NaHCO3 (1×), brine (1×)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (2.5×10 cm, 50% AcOEt/CH2Cl2)

출처 및 근거

ORD 기록
ord-9af68919aab545cf8c8d886551afd83e
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927688B2

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