Hydrochloric Acid → Ethyl 5-(4-Decanamidophenylsulfonamido)-1,3,4-thiadiazole-2-carboxylate

HRID 631067노트

반응식

HRID 631067 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]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[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]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[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 2756556Ethyl 5-amino-1,3,4-thiadiazole-2-carboxylateHCID 866543014-Decanamidobenzenesulfonyl chloride

생성물 1

HCID 53318403Ethyl 5-(4-Decanamidophenylsulfonamido)-1,3,4-thiadiazole-2-carboxylate수율 65%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 4-decanamidobenzenesulfonyl chloride (220 mg, 0.64 mmol) in pyridine (4 mL) was added ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate (100 mg, 0.58 mmol). The reaction mixture was stirred at room temperature for 4.5 h, then 2 M HCl (10 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate (3×30 mL). The organic extracts were washed with water (20 mL), brine (20 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography on silica gel (70-230 mesh) eluted with CH2Cl2:methanol 9:1 to give the product as a solid, mp 101-102° C., in 65% yield (183 mg, 0.38 mmol); 1H NMR (300 MHz, DMSO-d6) δ 0.83 (t, 3H, J=6.6 Hz), 1.22-1.32 (m, 15H), 1.56 (m, 2H), 2.31 (t, 2H, J=6.0 Hz), 4.33 (q, 2H, J=7.6 Hz), 7.71 (m, 4H), 10.19 (s, 1H); 13C NMR (75 MHz, DMSO-d6) δ 14.6, 14.6, 22.8, 25.6, 29.3, 29.4, 29.5, 29.6, 31.3, 31.9, 37.1, 62.8, 119.1, 127.6, 136.8, 143.2, 147.7, 159.2, 170.3, 172.5; MS (LCQ, ESI+) Calcd for C21H31N4O5S2 483.2. found 483.1 (M+H)+. HRMS (ESI+, m/z) Calcd for C21H31N4O5S2 483.1736. found 483.1728 (M+H)+.

후처리

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
  4. washThe organic extracts were washed with water (20 mL), brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (70-230 mesh)
  9. washeluted with CH2Cl2:methanol 9:1

출처 및 근거

ORD 기록
ord-bb8ed0c77a034ecfbce6beb528f8e104
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09320734B2

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