Hydrochloric Acid → HCID 20827737, compound

HRID 495612

Reaction equation

HRID 495612 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 20827737HCID 20827737, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-fdc240b87d614f63bb465c4f91210258
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Linked notes

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