Morpholine → Methyl 2-morpholinothiazole-4-carboxylate

HRID 1424339ノート

反応式

HRID 1424339 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 86700889Methyl 2-morpholinothiazole-4-carboxylate収率 93.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9af68919aab545cf8c8d886551afd83e
出典データセット
uspto-grants-2015_01
特許番号
US08927688B2

反応ノート

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