Pyridine → N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide

HRID 735889노트

반응식

HRID 735889 반응식
Cl.[CH3:2][NH:3][O:4][CH3:5].[F:6][C:7]([F:18])([F:17])[C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1.FC(F)(F)C1C=CC(C(O)=O)=CC=1.N1C=CC=CC=1>O=S(Cl)Cl.C(Cl)Cl>[CH3:5][O:4][N:3]([CH3:2])[C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:8]([C:7]([F:18])([F:17])[F:6])=[CH:9][CH:10]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 99664-(Trifluoromethyl)benzoic acidHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

생성물 1

HCID 14069348N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide수율 90%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 24386Thionyl Chloride용매

실험 절차

To a cold (0° C.) solution of N,O-dimethylhydroxylamine hydrochloride (2.5 g, 25.6 mmol) and 4-(trifluoromethyl)benzoyl chloride (prepared by refluxing a solution of 4-(trifluoromethyl)benzoic acid in SOCl2, 4.86 g, 23.3 mmol) in DCM (50 mL) was added dropwise pyridine (4.06 g, 51.26 mmol). The reaction mixture was stirred overnight and evaporated. The residue was dissolved in a mixture of DCM/Et2O (1/1) (45 mL) and brine (45 mL) was added. The aqueous layer was separated and extracted twice with DCM/Et2O (1/1) (45 mL). The combined organic layers were washed with brine (45 mL), dried over MgSO4, filtered and concentrated under vacuum to give the title compound as a yellow oil (4.88 g, 90%). 1H NMR (CDCl3, 300 MHz) δ 7.90-7.70 (m, 2H), 7.76-7.60 (m, 2H), 3.65-3.45 (m, 3H), 3.43-3.33 (m, 3H). HPLC (Condition A), Rt: 3.41 min (HPLC purity: 98.0%).

후처리

  1. customevaporated
  2. dissolutionThe residue was dissolved in a mixture of DCM/Et2O (1/1) (45 mL) and brine (45 mL)
  3. additionwas added
  4. customThe aqueous layer was separated
  5. extractionextracted twice with DCM/Et2O (1/1) (45 mL)
  6. washThe combined organic layers were washed with brine (45 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-214463a7d41a4a018c1a8626c07c39c0
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592477B2

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