Hydrochloric Acid → Ethyl 2-(5-(4-Decanamidophenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetate

HRID 631061

반응식

HRID 631061 반응식
[C:1]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[NH2:23][C:24]1[S:28][C:27]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:26][N:25]=1.Cl>N1C=CC=CC=1>[C:1]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:23][C:24]2[S:28][C:27]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:26][N:25]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 292304Ethyl 2-(5-amino-1,3,4-thiadiazol-2-yl)acetateHCID 866543014-Decanamidobenzenesulfonyl chloride

생성물 1

HCID 53325008Ethyl 2-(5-(4-Decanamidophenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetate수율 63%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of the 4-decanamidobenzenesulfonyl chloride (608 mg, 1.76 mmol) in pyridine (8 mL) was added ethyl 2-(5-amino-1,3,4-thiadiazol-2-yl)acetate (300 mg, 1.60 mmol). The reaction mixture was stirred at room temperature for 4.5 h, than 2 M HCl was added to quench the reaction. The mixture was extracted with ethyl acetate (3×40 mL). The organic extracts were washed with water (30 mL), brine (30 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography over silica gel (70-230 mesh) eluted with CH2Cl2:methanol 19:1 to give the product as a solid, mp 89-90° C., in 63% yield (500 mg, 1.01 mmol); 1H NMR (300 MHz, CDCl3) δ 0.87 (t, 3H, J=6.9 Hz), 1.25-1.34 (m, 15H), 1.65-1.76 (m, 2H), 2.39 (t, 2H, J=7.5 Hz), 3.87 (s, 2H), 4.24 (q, 2H, J=7.2 Hz), 7.58 (d, 2H, J=9.0 Hz), 7.74 (d, 2H, J=8.7 Hz); 13C NMR (75 MHz, DMSO-d6) δ 14.0, 14.0, 22.0, 25.5, 29.0, 29.0, 29.2, 31.3, 36.4, 37.9, 60.1, 118.9, 127.0, 139.4, 142.3, 154.0, 168.9, 169.9, 172.3; MS (LCQ, ESI+) Calcd for C22H33N4O5S2 497.2. found 497.1 (M+H)+. HRMS (ESI+, m/z) Calcd for C22H33N4O5S2 497.1875. found 497.1873 (M+H)+.

후처리

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionThe mixture was extracted with ethyl acetate (3×40 mL)
  5. washThe organic extracts were washed with water (30 mL), brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography over silica gel (70-230 mesh)
  10. washeluted with CH2Cl2:methanol 19:1

출처 및 근거

ORD 기록
ord-9f3101efdbfd4b0fb75949ccdf3d0bad
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09320734B2

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