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

HRID 220632

反応式

HRID 220632 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c680b3878a4b46bd8c355961ad235fae
出典データセット
uspto-grants-2012_06
特許番号
US08202895B2

関連ノート

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