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

HRID 495613Notes

Reaction equation

HRID 495613 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([C:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17]([N+:24]([O-])=O)=[CH:16][C:15]=1[N+:27]([O-])=O)[C:9](=[O:13])[O:10][CH2:11][CH3:12]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([C:14]1[C:19]([C:20]([F:21])([F:23])[F:22])=[CH:18][C:17]([NH2:24])=[CH:16][C:15]=1[NH2:27])[C:9](=[O:13])[O:10][CH2:11][CH3:12]

Participants

4

Reactant 1

HCID 20827737Ethyl 2-chlorophenyl[2,4-dinitro-6-(trifluoromethyl)phenyl]carbamate

Product 1

HCID 20827736Ethyl 2-chlorophenyl[2,4-diamino-6-(trifluoromethyl)phenyl]carbamateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-chlorophenyl[2,4-dinitro-6-(trifluoromethyl)phenyl]carbamate (0.645 g) was dissolved in ethyl acetate (100 ml), and to the solution was added 10% Pd—C (0.58 g). The reaction mixture was stirred under hydrogen atmosphere for 11 hours. The catalyst was filtered, and washed with ethyl acetate. The filtrate and washing were combined and concentrated in vacuo to give the title compound (0.543 g, 98%).

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with ethyl acetate
  3. washThe filtrate and washing
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55614f05576d45bc80a182b2496dd400
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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