Sodium Dithionite → t-Butyl N-[2-amino-5-(4-trifluoromethylphenoxy)phenyl]-N-methylcarbamate

HRID 2303905Notes

Reaction equation

HRID 2303905 reaction equation
C(=O)(O)[O-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:14][N:15]([C:23]1[CH:28]=[C:27]([O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=2)[CH:26]=[CH:25][C:24]=1[N+:40]([O-])=O)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]>O.O1CCOCC1>[NH2:40][C:24]1[CH:25]=[CH:26][C:27]([O:29][C:30]2[CH:31]=[CH:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=2)=[CH:28][C:23]=1[N:15]([CH3:14])[C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 18461356t-Butyl N-methyl-N-[2-nitro-5-(4-trifluoromethylphenoxy)phenyl]carbamate

Product 1

HCID 18461430t-Butyl N-[2-amino-5-(4-trifluoromethylphenoxy)phenyl]-N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Sodium bicarbonate (4.2 g) and sodium dithionite (3.5 g) were added to a solution of t-butyl N-methyl-N-[5-(4-trifluoromethylphenoxy)-2-nitrophenyl]carbamate in water/dioxane=1/5 (60 ml). The mixture was heated at reflux for 1 hour. At the end of this time the reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane/ethyl acetate=3/1-2/1 as the eluant to give the title compound (0.7 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customAt the end of this time the reaction mixture was partitioned between ethyl acetate and water
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-f824774552034b98aa13085ce5e2969e
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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