Hydrochloric Acid → 1-(4-Hydroxyphenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione

HRID 1616985ノート

反応式

HRID 1616985 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:19](=[O:20])[N:18]=[N:17][C:15]2=[O:16])=[CH:10][CH:9]=1.Cl>CC#N>[OH:7][C:1]1[CH:6]=[CH:5][C:4]([N:17]2[C:15](=[O:16])[N:14]([C:11]3[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=3)[C:19](=[O:20])[NH:18]2)=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 996PhenolHCID 779134-Phenyl-1,2,4-triazoline-3,5-dione

生成物 1

HCID 672581691-(4-Hydroxyphenyl)-4-phenyl-1,2,4-triazolidine-3,5-dione収率 15%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

To a solution of phenol (11.3 mg, 0.120 mmol) in 100 mM pH 7.0 NaH2PO4/Na2HPO4 buffer (3.0 mL)-CH3CN (3.0 mL) was slowly dropped the 0.3 M solution of PTAD 17a (0.442 mL, 0.132 mmol) in CH3CN at room temperature. The resulting solution was stirred at room temperature for 30 minutes. The reaction mixture was acidified with 1M HCl and extracted with ethyl acetate twice. The organic layer was dried over Na2SO4 and concentrated in vacuo. The obtained crude material was purified by flash column chromatography (ethyl acetate) to give para-adduct 27 (4.8 mg, 15%) and para-ortho-di-adduct 27′ (10.1 mg, 19%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 11.35 (br, 1H), 9.60 (s, 1H), 7.53-7.35 (m, 7H), 6.83 (m, 2H), 13C NMR (75 MHz, DMSO-d6): δ 156.11, 152.73, 150.41, 132.22, 129.22, 128.78, 128.66, 127.19, 122.99, 116.22. HRMS: calcd for C14H11N3O3 (MH+) 270.0873. found 270.0873.

後処理

  1. extractionextracted with ethyl acetate twice
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe obtained crude material
  5. customwas purified by flash column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-bfb3a288e50d49f6a258a63a18fbf492
出典データセット
uspto-grants-2014_07
特許番号
US08765920B2

反応ノート

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