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

HRID 1260893노트

반응식

HRID 1260893 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

(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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c0f803a604514148969246b33a2495ca
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470859B2

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