Dimethylamine, hydrochloride → 3-Cyano-4-dimethylamino-benzoic acid methyl ester

HRID 1041844ノート

反応式

HRID 1041844 の反応式
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([C:11]#[N:12])[CH:5]=1.Cl.[CH3:15][NH:16][CH3:17].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([N:16]([CH3:17])[CH3:15])=[C:6]([C:11]#[N:12])[CH:5]=1

参加物

5

反応物 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 45790123Methyl 3-cyano-4-fluorobenzoate

生成物 1

HCID 598476573-Cyano-4-dimethylamino-benzoic acid methyl ester収率 94%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a stirred solution of 24.0 g (134 mmol) 2 and 240 ml dimethylsulphoxid were added 13.2 g (161 mmol) dimethylamine hydrochloride and 38.9 g (281 mmol) potassium carbonate. The reaction mixture was stirred over night 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 product 3 was obtained in 94% yield (25.7 g, 126 mmol) and was used for the next step without purification.

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

出典と根拠

ORDレコード
ord-5b67f8c4f0ab4efc806f2630b0eb3865
出典データセット
uspto-grants-2013_10
特許番号
US08557776B2

反応ノート

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