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

HRID 240960

반응식

HRID 240960 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-600e11873279499c841ab360c962f1a4
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648116B2

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