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

HRID 240985노트

반응식

HRID 240985 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-343e1596dd9d4ccbbbfe7987515cf464
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648116B2

반응 노트

불러오는 중…