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

HRID 495618Notes

Reaction equation

HRID 495618 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][NH:5][C:6](=[O:10])[O:7][CH2:8][CH3:9].Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([N+:25]([O-:27])=[O:26])=[CH:18][C:17]=1[C:28]([F:31])([F:30])[F:29].[H-].[Na+].Cl>O1CCCC1>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][N:5]([C:16]1[C:17]([C:28]([F:30])([F:31])[F:29])=[CH:18][C:19]([N+:25]([O-:27])=[O:26])=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23])[C:6](=[O:10])[O:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 67851Benzene, 2-chloro-1,5-dinitro-3-(trifluoromethyl)-HCID 22327377Ethyl 2-chlorobenzylcarbamate

Product 1

HCID 20827734Ethyl 2-chlorobenzyl[2,4-dinitro-6-(trifluoromethyl)phenyl]carbamateYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-chlorobenzylcarbamate (809.9 mg) and 2-chloro-3,5-dinitrobenzotrifluoride (932.3 mg) were dissolved in tetrahydrofuran (20 ml), and to the solution was added sodium hydride (151.6 mg) under ice-cooling. The reaction mixture was heated at reflux for 5 hours. After allowing to cool, to the reaction mixture was added 1N hydrochloric acid (200 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, and then saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by silica gel column (100 g, hexane:ethyl acetate=5:1) to give the title compound (0.286 g, 19%).

Workup

  1. temperaturecooling
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 5 hours
  4. temperatureto cool, to the reaction mixture
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  7. dry with materialsaturated brine, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe resultant residue was purified by silica gel column (100 g, hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-0ea978e6d9b340d19412d2e14923630d
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

Loading…