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

HRID 735889

反応式

HRID 735889 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 24386Thionyl Chloride溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-214463a7d41a4a018c1a8626c07c39c0
出典データセット
uspto-grants-2009_09
特許番号
US07592477B2

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