Diisopropylethylamine → 2-(5-Dodecyl-[1,2,4]oxadiazol-3-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide

HRID 264133

반응식

HRID 264133 반응식
[C:1](Cl)(=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].ON[N:18]=[CH:19][CH:20]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:21]([NH:23][C:24]1[C:29]([O:30][CH3:31])=[CH:28][C:27]([O:32][CH3:33])=[CH:26][C:25]=1[O:34][CH3:35])=[O:22].CC[N:44](C(C)C)C(C)C>C1COCC1>[CH2:2]([C:1]1[O:14][N:44]=[C:19]([CH:20]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:21]([NH:23][C:24]2[C:29]([O:30][CH3:31])=[CH:28][C:27]([O:32][CH3:33])=[CH:26][C:25]=2[O:34][CH3:35])=[O:22])[N:18]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 87288Tridecanoyl chlorideHCID 70113100alpha-[(hydroxyamino)iminomethyl]-N-(2,4,6-trimethoxyphenyl)-benzeneacetamide

생성물 1

HCID 108401012-(5-Dodecyl-[1,2,4]oxadiazol-3-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide수율 62%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Tridecanoyl chloride (15.08 g, 0.061 mol) was added to a mixture of α-[(hydroxyamino)iminomethyl]-N-(2,4,6-trimethoxyphenyl)-benzene acetamide (19.8 g, 0.055 mol), Hunig's base (10.6 mL, 0.061 mol), and THF (200 mL). The mixture was stirred in THF at room temperature for 2 hours, then concentrated in vacuo and dissolved in glacial acetic acid (50 mL) and refluxed for 2 hours, then concentrated in vacuo, azeotroped with toluene (2×250 mL), and columned on silica gel eluting with 35% ethyl acetate in hexanes to yield a white solid (12.1 g, 62%). %(found): C, 68.93; H, 7.96; N, 7.54.

후처리

  1. concentrationconcentrated in vacuo
  2. dissolutiondissolved in glacial acetic acid (50 mL)
  3. temperaturerefluxed for 2 hours
  4. concentrationconcentrated in vacuo
  5. customazeotroped with toluene (2×250 mL)

출처 및 근거

ORD 기록
ord-a322a9773da24e4bb2aab4466ab1a1dc
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646170

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