Triethylamine → HCID 21090614, 화합물

HRID 350963노트

반응식

HRID 350963 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 21090614HCID 21090614, 화합물수율 44.4%

시약·촉매·용매 2

HCID 24085Mercuric Chloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-bee518b7a7c5416ca27f0f29db853639
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183302B2

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