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Dimethylamine, hydrochloride → 5-Dimethylamino-2-trifluoromethyl-benzoic acid methyl ester

HRID 1041873
ノート
印刷プレビュー

反応式

HRID 1041873 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12].Cl.[CH3:17][NH:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N:18]([CH3:19])[CH3:17])[CH:7]=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 46311153Methyl 5-fluoro-2-(trifluoromethyl)benzoate

生成物 1

HCID 669091775-Dimethylamino-2-trifluoromethyl-benzoic acid methyl ester収率 72%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of 4.48 g (22.5 mmol) 5-Fluoro-2-trifluoromethyl-benzoic acid methyl ester (Rarechem) and 60.0 ml dimethylsulphoxid were added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture was stirred for 8 h at 60° C. in an autoclave and was reduced with high vacuum rotation evaporator at 65° C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude was purified by column chromatography and the desired product 15a was obtained in 72% yield (4.00 g, 16.2 mmol).

後処理

  1. customwas reduced with high vacuum rotation evaporator at 65° C
  2. additionThe residue was diluted with dichloromethane
  3. washwashed twice with water
  4. extractionThe combined water phases were extracted with dichloromethane
  5. washThe combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated
  8. customThe oily crude was purified by column chromatography

出典と根拠

ORDレコード
ord-1daa148fcf1442f69ede2034710e96be
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08557776B2

反応ノート

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