Sodium Bicarbonate → Ethyl 4-chlorophenyl[2,4-diamino-6-(trifluoromethyl)phenyl]carbamate

HRID 495643Notes

Reaction equation

HRID 495643 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17]([N+:24]([O-])=O)=[CH:16][C:15]=2[N+:27]([O-])=O)[C:9](=[O:13])[O:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>CO.[Cl-].[Ti+3].[Cl-].[Cl-]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:14]2[C:19]([C:20]([F:23])([F:21])[F:22])=[CH:18][C:17]([NH2:24])=[CH:16][C:15]=2[NH2:27])[C:9](=[O:13])[O:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 20827748HCID 20827748, compound

Product 1

HCID 20827747Ethyl 4-chlorophenyl[2,4-diamino-6-(trifluoromethyl)phenyl]carbamateYield 82.3%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolvent

Procedure

Ethyl 4-chlorophenyl[2,4-dinitro-6-(trifluoromethyl)phenyl]carbamate (1.7323 g) was dissolved in methanol (100 ml), and to the solution was added titanium(III) chloride solution (36.967 g) under ice-cooling. The reaction mixture was stirred for 2 hours. To the reaction mixture was added saturated aqueous sodium bicarbonate solution (800 ml), and the mixture was extracted 2 times 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 (70 g, CHCl3:methanol=10:1) to give the title compound (1.2292 g, 82%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted 2 times with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by silica gel column (70 g, CHCl3:methanol=10:1)

Sources & evidence

ORD record
ord-488d1e387b06435c8b7d2c9d00ad2519
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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