Hydrochloric Acid → HCID 20827730, compound

HRID 495648Notes

Reaction equation

HRID 495648 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:14])[O:11][CH2:12][CH3:13].[H-].[Na+].Cl[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21]([N+:27]([O-:29])=[O:28])=[CH:20][C:19]=1[C:30]([F:33])([F:32])[F:31].Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]([C:18]1[C:19]([C:30]([F:32])([F:33])[F:31])=[CH:20][C:21]([N+:27]([O-:29])=[O:28])=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[C:10](=[O:14])[O:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 67851Benzene, 2-chloro-1,5-dinitro-3-(trifluoromethyl)-HCID 80626Carbamic acid, (2,4-dichlorophenyl)-, ethyl ester

Product 1

HCID 20827730HCID 20827730, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2,4-dichlorophenylcarbamate (1.206 g) was dissolved in tetrahydrofuran (15 ml), and to the solution were added sodium hydride (206.0 mg) and 2-chloro-3,5-dinitrobenzotrifluoride (1.161 g). The reaction mixture was stirred at room temperature for 4 hours. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by silica gel column (75 g, hexane:ethyl acetate=5:1) to give the title compound (1.4490 g, 72%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by silica gel column (75 g, hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-c12b8cda65d84a69b8114dab87462ef2
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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