Aniline → 4-Nitro-3-phenylaminobenzonitrile

HRID 242800ノート

反応式

HRID 242800 の反応式
F[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6].[C:13]1([NH2:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CS(C)=O>[N+:10]([C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[NH:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O-:12])=[O:11]

参加物

4

反応物 2

HCID 6115AnilineHCID 27833993-Fluoro-4-nitrobenzonitrile

生成物 1

HCID 681579814-Nitro-3-phenylaminobenzonitrile収率 98.2%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

A suspension of 3-fluoro-4-nitrobenzonitrile (1.66 g, 10.0 mmol) in DMSO (5 mL) was purged with a stream of argon prior to addition of phenylamine (1.82 mL, 20.0 mmol) and then the mixture was stirred at 120° C. for 1 h under an argon atmosphere. After cooling to RT, the reaction mixture was partitioned between EtOAc (75 mL) and an aqueous solution of KHSO4 (100 mL). The organic layer was then washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was triturated with diethyl ether affording 4-Nitro-3-phenylaminobenzonitrile as red crystals (2.35 g, 98%). 1H NMR (CDCl3, 400 MHz): δ 9.48 (1H, bs), 8.29 (1H, d, J=8.76 Hz), 7.53-7.40 (3H, m), 7.35 (1H, t, J=7.52 Hz), 7.29-7.22 (2H, m), 6.97 (1H, d, J=8.79 Hz).

後処理

  1. customwas purged with a stream of argon
  2. temperatureAfter cooling to RT
  3. customthe reaction mixture was partitioned between EtOAc (75 mL)
  4. washThe organic layer was then washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was triturated with diethyl ether

出典と根拠

ORDレコード
ord-9d8f1c53e2a64e629f2c33cfb962b937
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

読み込み中…