Thionyl Chloride → Benzoic acid, 3-chloro-5-cyano-, methyl ester

HRID 1260893ノート

反応式

HRID 1260893 の反応式
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([Cl:14])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=O.S(Cl)(Cl)=O>CN(C)C=O>[Cl:14][C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([C:2]#[N:1])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 58963003Methyl 3-carbamoyl-5-chlorobenzoate

生成物 1

HCID 21942517Benzoic acid, 3-chloro-5-cyano-, methyl ester収率 57.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

(Step 1) To a solution of methyl 3-(aminocarbonyl)-5-chlorobenzoate (2.2 g) in N,N-dimethylformamide (15 ml) was added thionyl chloride (2 ml) at 0° C., and the mixture was stirred at 80° C. for 1 hr. The reaction solution was quenched with ice and extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogen carbonate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=1:1) to give methyl 3-chloro-5-cyanobenzoate (1.15 g) as a white solid.

後処理

  1. customThe reaction solution was quenched with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with aqueous sodium hydrogen carbonate solution
  4. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionthe obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=1:1)

出典と根拠

ORDレコード
ord-c0f803a604514148969246b33a2495ca
出典データセット
uspto-grants-2013_06
特許番号
US08470859B2

反応ノート

読み込み中…