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Triethylamine → 3-(Difluoromethyl)-N-methoxy-1-methyl-N-(1-methyl-2-(2,4,6-trichlorophenyl)ethyl)-1H-pyrazole-4-carboxamide

HRID 2381251
ノート
印刷プレビュー

反応式

HRID 2381251 の反応式
[CH3:1][O:2][NH:3][CH:4]([CH3:15])[CH2:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=1[Cl:14].C(N(CC)CC)C.[F:23][CH:24]([F:34])[C:25]1[C:29]([C:30](Cl)=[O:31])=[CH:28][N:27]([CH3:33])[N:26]=1>ClCCl.O>[CH3:1][O:2][N:3]([CH:4]([CH3:15])[CH2:5][C:6]1[C:7]([Cl:14])=[CH:8][C:9]([Cl:13])=[CH:10][C:11]=1[Cl:12])[C:30]([C:29]1[C:25]([CH:24]([F:34])[F:23])=[N:26][N:27]([CH3:33])[CH:28]=1)=[O:31]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 58443683N-methoxy-1-(2,4,6-trichlorophenyl)propan-2-amine

生成物 1

HCID 569334113-(Difluoromethyl)-N-methoxy-1-methyl-N-(1-methyl-2-(2,4,6-trichlorophenyl)ethyl)-1H-pyrazole-4-carboxamide収率 49.8%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of O-Methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)-ethyl]-hydroxylamine (0.65 g, 2.4 mmol) prepared as described in example P15d, in dichloromethane (5 ml) was added triethylamine (0.844 ml, 6.0 mmol) followed by drop wise addition of a solution 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (0.519 g, 2.67 mmol) in dichloromethane at 0° C. After complete addition of acid chloride the mixture was stirred 18 hours at ambient temperature. When the TLC confirmed completion of the reaction, the reaction mass was diluted with water and extracted with dichloromethane (3×60 ml). The combined dichloromethane layer were washed with 2N HCl, followed by saturated NaHCO3, then with water and finally with brine solution before drying over sodium sulfate and evaporation of the solvent. The resulting crude mass was purified by column chromatography using 60-120μ mesh silica gel and product collected at 30% ethyl acetate in hexane as eluent to give 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-methyl-2-(2,4,6-trichloro-phenyl)-ethyl]-amide (0.51 g, 49%) as off white solid. m.p: 110-112° C.

後処理

  1. customcompletion of the reaction
  2. extractionextracted with dichloromethane (3×60 ml)
  3. washThe combined dichloromethane layer were washed with 2N HCl
  4. dry with materialwith water and finally with brine solution before drying over sodium sulfate and evaporation of the solvent
  5. customThe resulting crude mass was purified by column chromatography
  6. customcollected at 30% ethyl acetate in hexane as eluent

出典と根拠

ORDレコード
ord-500499bc962b46ed9679f64cb45bd270
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08258169B2

反応ノート

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