Ammonium Chloride → 5,6-difluoro-N1-(2-fluoro-4-iodophenyl)-3-methoxybenzene-1,2-diamine

HRID 889507ノート

反応式

HRID 889507 の反応式
[Cl-].[NH4+].[F:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([O:11][CH3:12])=[C:6]([N+:13]([O-])=O)[C:5]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=1[F:24]>C(O)C.[Fe]>[F:10][C:9]1[C:4]([F:3])=[C:5]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=2[F:24])[C:6]([NH2:13])=[C:7]([O:11][CH3:12])[CH:8]=1

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 593863122,3-Difluoro-N-(2-fluoro-4-iodophenyl)-5-methoxy-6-nitroaniline

生成物 1

HCID 532609665,6-difluoro-N1-(2-fluoro-4-iodophenyl)-3-methoxybenzene-1,2-diamine収率 90.3%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

Ammonium chloride (1.18 g, 20.16 mmol) and iron powder (1.15 g, 21.44 mmol) were added to a stirred solution of (2,3-difluoro-5-methoxy-6-nitro-phenyl)-(2-fluoro-4-iodo-phenyl)-amine (0.57 g, 1.34 mmol) in ethanol (20 mL). The mixture was stirred at reflux for 16 hours, cooled to room temperature, filtered over celite and the filtrate concentrated to dryness. The resulting residue was taken into ethyl acetate, washed with water, dried over sodium sulfate and further purified by crystallization from ethanol to provide the product as an off-white solid (0.47 g, 90.3%). M−H+: 393.2. 1H NMR (DMSO, 300 MHz): 3.76 (s, 3H); 6.1 (t, 1H); 6.8-7.0 (m, 1H); 7.2 (d, 1H); 7.35 (s, 1H); 7.42 (d, 1H).

後処理

  1. temperatureat reflux for 16 hours
  2. filtrationfiltered over celite
  3. concentrationthe filtrate concentrated to dryness
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customfurther purified by crystallization from ethanol

出典と根拠

ORDレコード
ord-abfbd37b36244d1b869eb25034e99563
出典データセット
uspto-grants-2012_08
特許番号
US08252842B2

反応ノート

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