Sodium Bicarbonate → Ethyl 2-amino-4-cyano-6-(trifluoromethyl)phenyl(2-chlorobenzyl)carbamate

HRID 495633Notes

Reaction equation

HRID 495633 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]([C:11]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][C:14]([C:21]#[N:22])=[CH:13][C:12]=1[N+:23]([O-])=O)[C:6](=[O:10])[O:7][CH2:8][CH3:9].C(=O)(O)[O-].[Na+]>CO.[Cl-].[Ti+3].[Cl-].[Cl-]>[NH2:23][C:12]1[CH:13]=[C:14]([C:21]#[N:22])[CH:15]=[C:16]([C:17]([F:19])([F:20])[F:18])[C:11]=1[N:5]([CH2:4][C:3]1[CH:26]=[CH:27][CH:28]=[CH:29][C:2]=1[Cl:1])[C:6](=[O:10])[O:7][CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 69744412Ethyl 2-chlorobenzyl[4-cyano-2-nitro-6-(trifluoromethyl)phenyl]carbamate

Product 1

HCID 22327355Ethyl 2-amino-4-cyano-6-(trifluoromethyl)phenyl(2-chlorobenzyl)carbamateYield 113.7%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolvent

Procedure

Ethyl 2-chlorobenzyl[4-cyano-2-nitro-6-(trifluoromethyl)phenyl]carbamate (298.4 mg) was dissolved in methanol (30 ml), and to the solution were added titanium(III) chloride solution (6.672 g) under ice-cooling. After stirring for 20 minutes, to the reaction mixture was added saturated aqueous sodium bicarbonate solution, 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 to give the title compound (315.4 mg, quantitative yield).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e8a187162164f62a2c57cbea959b50b
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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