Nitric Acid → 1-Acetamido-2-nitro-3,5-bis(trifluoromethyl)benzene

HRID 439524

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HRID 439524 반응식
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[CH:6]=1)(=[O:3])[CH3:2].[N+:19]([O-])([OH:21])=[O:20]>OS(O)(=O)=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:15]([F:16])([F:17])[F:18])[CH:8]=[C:9]([C:11]([F:13])([F:14])[F:12])[C:10]=1[N+:19]([O-:21])=[O:20])(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 7236003',5'-Bis(trifluoromethyl)acetanilide

생성물 1

HCID 199585741-Acetamido-2-nitro-3,5-bis(trifluoromethyl)benzene

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

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온도
0 °C

실험 절차

To a solution of 1-acetamido-3,5-bis(trifluoromethyl)benzene (400 mg, 1.37 mmol) in concentrated H2SO4 (3 mL) at 0° C. was added dropwise 70% HNO3 (0.4 mL, Baker). The mixture was stirred at 0° C. for 0.5 h, then at room temperature for 3 h and it was poured into ice water (10 g). The precipitate was collected by filtration, affording 400 mg of crude product which contained two compounds by 1H NMR. It was separated on a column of silica gel, eluted with chloroform, to afford 134 mg of pure 1-acetamido-2-nitro-3,5-bis(trifluoromethyl)benzene as white long needles. mp: 190°-2° C., 1H NMR (CDCl3): δ2.226 (s, 3H), 7.765 (s, 1H), 7.978 (s, 1H); 8.918 (s, 1H).

후처리

  1. waitat room temperature for 3 h
  2. filtrationThe precipitate was collected by filtration
  3. customaffording 400 mg of crude product which
  4. customIt was separated on a column of silica gel
  5. washeluted with chloroform

출처 및 근거

ORD 기록
ord-055b6a44d5624394855b79eefdce8a77
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05514680

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