Hydrochloric Acid → 2-(2-Nitro-phenylamino)-5-trifluoromethyl-benzonitrile

HRID 131318

反応式

HRID 131318 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[N+:7]([C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12])([O-:9])=[O:8].F[C:18]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:19]=1[C:20]#[N:21].Cl>CN(C=O)C>[N+:7]([C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH:12][C:18]1[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:22][C:19]=1[C:20]#[N:21])([O-:9])=[O:8]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 69462-NitroanilineHCID 10796Cesium carbonateHCID 5210162-Fluoro-5-(trifluoromethyl)benzonitrile

生成物 1

HCID 210934552-(2-Nitro-phenylamino)-5-trifluoromethyl-benzonitrile収率 80%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Add cesium carbonate (1.3 g, 4 mmol) to a solution of 2-nitro-aniline (276 mg, 2 mmol) and 2-fluoro-5-trifluoromethyl-benzonitrile (378 mg, 2 mmol) in DMF (10 mL) at room temperature then stir the resulting dark red solution at room temperature for 16 hours and 2 hours at 50° C. Cool down and pour into a mixture of ice and concentrated hydrochloric acid (50 mL, v/v). Extract the aqueous phase with dichloromethane (3×300 mL), wash with water and brine and dry over MgSO4 to yield the title compound as a yellow solid (480 mg, 80%): mp 160-161° C.; 1H NMR (CDCl3) δ 7.14 (ddd, 1H), 7.48 (dd, 1H), 7.58 (dd, 1H), 7.60 (d, 1H), 7.76 (dd, 1H), 7.92 (d, 1H), 8.27 (dd, 1H), 9.63 (bs, 1H). MS (ESI/neg) m/z (rel intensity) 306.1 (100).

後処理

  1. custom2 hours
  2. customat 50° C
  3. temperatureCool down
  4. extractionExtract the aqueous phase with dichloromethane (3×300 mL)
  5. washwash with water and brine
  6. dry with materialdry over MgSO4

出典と根拠

ORDレコード
ord-09aab4e9a1164eb395103bff6141f7df
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

関連ノート

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