Tetrahydrofuran → 4-((2,6-Dinitrophenyl)amino)resorcinol

HRID 1456935

反応式

HRID 1456935 の反応式
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].Cl.[NH2:15][C:16]1[CH:22]=[CH:21][C:19]([OH:20])=[CH:18][C:17]=1[OH:23].O1CCCC1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[N+:11]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:15][C:16]1[CH:22]=[CH:21][C:19]([OH:20])=[CH:18][C:17]=1[OH:23])([O-:13])=[O:12]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 118141-Chloro-2,6-dinitrobenzeneHCID 81531DiisopropylethylamineHCID 134088224-Aminobenzene-1,3-diol hydrochloride

生成物 1

HCID 540632544-((2,6-Dinitrophenyl)amino)resorcinol収率 79.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

6 g (30 mmol) of 1-chloro-2,6-dinitrobenzene and 4.8 g (30 mmol) of 4-aminoresorcinol hydrochloride were added to 300 ml of a mixture of tetrahydrofuran with dimethylformamide (1:1). After adding 7.8 g (60 mmol) of N,N-diisopropylethylamine thereto, the obtained mixture was stirred at room temperature for 24 hours. Then the solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate and washed with a saturated aqueous solution of sodium chloride. Then it was dried over magnesium sulfate and concentrated and the residue was purified by silica gel column chromatography. Thus 6.95 g of 4-[(2,6-dinitrophenyl)amino]resorcinol was obtained. This product was dissolved in 125 ml of dimethylformamide and 25 ml of N,N-diisopropylethylamine was added thereto. After heating at 100° C. for 2 hours, the reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, dried over magnesium sulfate and concentrated to dryness. Thus 5.4 g of the title compound was obtained.

後処理

  1. distillationThen the solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialThen it was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-98a255e7e460486b95536713285ef828
出典データセット
uspto-grants-1998_12
特許番号
US05846969

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