Nitromethane → tert-Butyl {2-nitro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

HRID 220632

반응식

HRID 220632 반응식
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5](/[CH:9]=[N:10]/[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:6]=[CH:7][CH:8]=1.C(N(CC)C(C)C)(C)C.[N+:29]([CH3:32])([O-:31])=[O:30]>C(OCC)(=O)C>[N+:29]([CH2:32][CH:9]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15])[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:18])([F:19])[F:1])[CH:4]=1)([O-:31])=[O:30]

참가 물질

5

반응물 3

HCID 6375NitromethaneHCID 81531DiisopropylethylamineHCID 46855703tert-butyl (NE)-N-[[3-(trifluoromethyl)phenyl]methylidene]carbamate

생성물 1

HCID 59536870tert-Butyl {2-nitro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Of the compound from Example 11A, 3.6 g (13.17 mmol) were introduced in 26 ml of nitromethane and admixed with 0.69 ml (3.95 mmol) of N,N-diisopropylethylamine. The mixture was stirred at RT for 2 h. The reaction mixture was diluted with ethyl acetate and washed in succession twice each with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, and then with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated on a rotary evaporator. The residue (about 5 g) was dissolved in 15 ml of isopropanol at reflux. After cooling, the precipitated product was isolated by filtration, washed with a little isopropanol and sucked dry. After further drying in an HV, the title compound was obtained: 2.26 g (51% of theory).

후처리

  1. washwashed in succession twice each with 1N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialwith saturated aqueous sodium chloride solution, dried over sodium sulphate
  3. concentrationconcentrated on a rotary evaporator
  4. dissolutionThe residue (about 5 g) was dissolved in 15 ml of isopropanol
  5. temperatureat reflux
  6. temperatureAfter cooling
  7. customthe precipitated product was isolated by filtration
  8. washwashed with a little isopropanol
  9. customsucked dry
  10. customAfter further drying in an HV

출처 및 근거

ORD 기록
ord-c680b3878a4b46bd8c355961ad235fae
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202895B2

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