Hydrochloric Acid → Ethyl 2-chlorophenyl[2,4-dinitro-6-(trifluoromethyl)phenyl]carbamate

HRID 495612

反応式

HRID 495612 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12].[H-].[Na+].Cl[C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20]([N+:26]([O-:28])=[O:27])=[CH:19][C:18]=1[C:29]([F:32])([F:31])[F:30].Cl>COCCOCCOC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([C:17]1[C:18]([C:29]([F:31])([F:32])[F:30])=[CH:19][C:20]([N+:26]([O-:28])=[O:27])=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])[C:9](=[O:13])[O:10][CH2:11][CH3:12]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 67851Benzene, 2-chloro-1,5-dinitro-3-(trifluoromethyl)-HCID 528085Ethyl 2-chlorophenylcarbamate

生成物 1

HCID 20827737Ethyl 2-chlorophenyl[2,4-dinitro-6-(trifluoromethyl)phenyl]carbamate収率 93%

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

実験手順

Ethyl 2-chlorophenylcarbamate (62.6 mg) was dissolved in diglyme (1 ml), and to the solution were added sodium hydride (12.6 mg) and 2-chloro-3,5-dinitrobenzotrifluoride (77.1 mg). The reaction mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and then saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by preparative TLC (2 mm, 20×20 cm, hexane:ethyl acetate=3:1) to give the title compound (114.8 mg, 93%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution
  3. dry with materialsaturated brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by preparative TLC (2 mm, 20×20 cm, hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-fdc240b87d614f63bb465c4f91210258
出典データセット
uspto-grants-2005_09
特許番号
US06939887B2

関連ノート

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