2-(4-{[5-Chloro-2-nitro-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl (4-methylphenyl)sulfonylcarbamate → 2-(4-{[2-Amino-5-chloro-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl (4-methylphenyl)sulfonylcarbamate

HRID 724127Notes

Reaction equation

HRID 724127 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12](=[O:37])[O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]3[CH:28]=[C:27]([Cl:29])[C:26]([C:30]([F:33])([F:32])[F:31])=[CH:25][C:24]=3[N+:34]([O-])=O)=[CH:18][CH:17]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12](=[O:37])[O:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23]3[CH:28]=[C:27]([Cl:29])[C:26]([C:30]([F:33])([F:31])[F:32])=[CH:25][C:24]=3[NH2:34])=[CH:20][CH:21]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 866115002-(4-{[5-Chloro-2-nitro-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl (4-methylphenyl)sulfonylcarbamate

Product 1

HCID 866115012-(4-{[2-Amino-5-chloro-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl (4-methylphenyl)sulfonylcarbamateYield 102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-(4-{[5-chloro-2-nitro-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl (4-methylphenyl)sulfonylcarbamate (step 1, 1.51 g, 2.71 mmol) in methanol (250 ml) was added 5% platinum-sulfided on carbon (600 mg). The mixture was stirred at room temperature for 5 h under hydrogen atmosphere (4 atm). The palladium catalyst was removed by filtration and washed with dichloromethane (100 ml). The filtrate was concentrated under reduced pressure to afford 1.46 g (99%) of the title compound as a brown oil.

Workup

  1. customThe palladium catalyst was removed by filtration
  2. washwashed with dichloromethane (100 ml)
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b31361c021b345618d28d2b6815a9fdf
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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