Ethyl Acetate → 3,5,6-trifluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine

HRID 2357398

反応式

HRID 2357398 の反応式
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:15]([N+:16]([O-])=O)=[C:14]([F:19])[CH:13]=[C:12]([F:20])[C:11]=1[F:21].[Cl-].[NH4+].CCOC(C)=O>CCO.[Fe]>[F:21][C:11]1[C:12]([F:20])=[CH:13][C:14]([F:19])=[C:15]([NH2:16])[C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 574300722,3,5-trifluoro-N-(2-fluoro-4-iodophenyl)-6-nitroaniline

生成物 1

HCID 593863433,5,6-trifluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine収率 66.4%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

To the stirred solution of (2-fluoro-4-iodo-phenyl)-(2,3,5-trifluoro-6-nitro-phenyl)-amine 3 (5.2 gm, 12.62 mmol) in EtOH (200 ml), ammonium chloride (10.12 gm, 189.3 mmol) and iron powder (10.57 gm, 189.3 mmol) was added. This reaction mixture was kept stirring at reflux for 16 hours. Reaction mixture was allowed to cool and was filtered over celite and concentrated to dryness. The residue obtained was taken into EtOAc and was washed with water. The EtOAc layer was dried over sodium sulfate and further purified by crystallization from EtOH to provide off-white solid (3.2 gm, yield: 66.39%). M−H+: 381.1. 1H NMR (DMSO, 300 MHz): 5.0 (s, 2H); 6.2 (t, 1H); 7.2-7.3 (m, 2H); 7.45 (s, 1H); 7.5 (d, 1H).

後処理

  1. temperatureat reflux for 16 hours
  2. customReaction mixture
  3. temperatureto cool
  4. filtrationwas filtered over celite and
  5. concentrationconcentrated to dryness
  6. customThe residue obtained
  7. washwas washed with water
  8. dry with materialThe EtOAc layer was dried over sodium sulfate
  9. customfurther purified by crystallization from EtOH

出典と根拠

ORDレコード
ord-62daeff3ea2345029645b6d41213ed8e
出典データセット
uspto-grants-2010_07
特許番号
US07759518B2

関連ノート

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