Imidazole → HCID 59333299、化合物

HRID 1893476ノート

反応式

HRID 1893476 の反応式
[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[NH:16]1[CH:20]=[CH:19][N:18]=[CH:17]1.C(N(CC)C(C)C)(C)C>C(#N)C>[Br:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[CH:7]=1

参加物

5

反応物 3

HCID 795ImidazoleHCID 81531DiisopropylethylamineHCID 594197851-Bromo-5-fluoro-4-nitro-2-(trifluoromethyl)benzene

生成物 1

HCID 59333299HCID 59333299、化合物収率 86.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

A mixture of 1-bromo-5-fluoro-4-nitro-2-(trifluoromethyl)benzene (16.0 g, 0.0556 mol), imidazole (4.0 g, 0.0588 mol) and N,N-diisopropylethylamine (10.1 mL, 0.0582 mol) in acetonitrile (160 mL) is stirred under nitrogen for 1.5 hour at 80° C. After concentration of the reaction mixture, the residue is partitioned between water and ethyl acetate. The aqueous phase is extracted with ethyl acetate, the combined organic phases are washed in turn with a saturated solution of ammonium chloride, brine and dried over sodium sulfate. Concentration and purification by cake filtration over silica gel, eluting with a mixture of ethyl acetate and cyclohexane from 2/8 to 1/1 affords the title compound as a yellow solid (16.1 g, 86.2%)

後処理

  1. customAfter concentration of the reaction mixture, the residue is partitioned between water and ethyl acetate
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. washthe combined organic phases are washed in turn with a saturated solution of ammonium chloride, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration and purification
  6. filtrationby cake filtration over silica gel
  7. washeluting with a mixture of ethyl acetate and cyclohexane from 2/8 to 1/1

出典と根拠

ORDレコード
ord-4242963cda404db48465ed51562c1e37
出典データセット
uspto-grants-2013_08
特許番号
US08513250B2

反応ノート

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