Triethylamine → HCID 21090614、化合物

HRID 350963ノート

反応式

HRID 350963 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11](=[O:12])[CH2:10][S:9][C:8]1=S.[N:14]1([C:20]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.CCN(CC)CC>C1COCC1.[Hg](Cl)Cl>[N:14]1([C:20]2[CH:21]=[CH:22][C:23]([N:24]=[C:8]3[N:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[C:11](=[O:12])[CH2:10][S:9]3)=[CH:25][CH:26]=2)[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 223458353-(Pyridin-2-yl)-2-sulfanylidene-1,3-thiazolidin-4-one

生成物 1

HCID 21090614HCID 21090614、化合物収率 44.4%

試薬・触媒・溶媒 2

HCID 24085Mercuric Chloride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

3-(2-pyridyl)-2-thioxo-thiazolidin-4-one (1.1 g, 5.3 mmol, 1.0 equiv), prepared as described in J. Chem. Soc. (1956) 1644, was dissolved in 30 ml THF and charged with 4-morpholin-4-yl aniline (0.94 g, 5.28 mmol, 1.0 equiv) and Et3N (1.47 ml, 10.6 mmol, 2.0 equiv). Mercury (II) chloride (1.4 g, 5.28 mmol, 1.0 equiv) was added in one portion as a solid, and the heterogeneous mixture was stirred at ambient temperature overnight. The reaction mixture was filtered through Celite, and the filtrate was partitioned between EtOAc and saturated NH4Cl. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. Flash chromatography (40% to 100% EtOAc in hexanes, silica) afforded 0.83 g (44%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 8.70 (m, 1H), 7.90 (m, 1H), 7.37–7.44 (m, 2H), 3.99 (s, 2H), 3.84 (m, 4H), 3.11 (m, 4H); MS (ESI) m/z=355.3 (MH+).

後処理

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate was partitioned between EtOAc and saturated NH4Cl
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-bee518b7a7c5416ca27f0f29db853639
出典データセット
uspto-grants-2007_02
特許番号
US07183302B2

反応ノート

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