Phenethyl bromide → Methyl 4-nitro-1-phenethyl-1H-pyrazole-3-carboxylate

HRID 547506ノート

反応式

HRID 547506 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][NH:7][N:6]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][N:7]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:6]=1)=[O:4]

参加物

5

反応物 3

HCID 7666Phenethyl bromideHCID 10796Cesium carbonateHCID 178499180HCID 178499180、化合物

生成物 1

HCID 67198071Methyl 4-nitro-1-phenethyl-1H-pyrazole-3-carboxylate収率 65.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

430 mg (2.5 mM) of 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester was dissolved in 4 ml of N,N-dimethylformamide, to which 0.41 ml (3 mM) of (2-bromoethyl)benzene and 1.6 g (5.0 mM) of cesium carbonate were added dropwise, and the mixture was stirred under a nitrogen atmosphere for a day. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=5:1), to obtain 506 mg (65.5%) of the title compound and 218 mg (31.2%) of the compound of Preparative Example 10.

後処理

  1. additionwere added dropwise
  2. distillationThe solvent was distilled off under reduced pressure
  3. extractionthe resultant was extracted with ethyl acetate and brine
  4. dry with materialThe organic solvent layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled under reduced pressure
  7. customThe resulting impure compound was purified by column chromatography (hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-d54ff581a1bb495986f13fc1ec59049e
出典データセット
uspto-grants-2011_05
特許番号
US07939550B2

反応ノート

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