p-Toluenesulfonyl isocyanate → 2-(4-{[5-Chloro-2-nitro-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl (4-methylphenyl)sulfonylcarbamate

HRID 724126Notes

Reaction equation

HRID 724126 reaction equation
[Cl:1][C:2]1[C:3]([C:21]([F:24])([F:23])[F:22])=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=2)[CH:7]=1.[C:25]1([CH3:37])[CH:30]=[CH:29][C:28]([S:31]([N:34]=[C:35]=[O:36])(=[O:33])=[O:32])=[CH:27][CH:26]=1>ClCCl>[CH3:37][C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:34][C:35](=[O:36])[O:17][CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:6]3[CH:7]=[C:2]([Cl:1])[C:3]([C:21]([F:22])([F:23])[F:24])=[CH:4][C:5]=3[N+:18]([O-:20])=[O:19])=[CH:10][CH:11]=2)(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 218764722-(4-{[5-Chloro-2-nitro-4-(trifluoromethyl)phenyl]amino}phenyl)ethanol

Product 1

HCID 866115002-(4-{[5-Chloro-2-nitro-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl (4-methylphenyl)sulfonylcarbamateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-{[5-chloro-2-nitro-4-(trifluoromethyl)phenyl]amino}phenyl)ethanol (step 2 of Example 104, 1.0 g, 2.77 mmol) in dichloromethane (45 ml) was added p-toluenesulfonyl isocyanate (574 mg, 2.91 mmol), and the mixture was stirred at room temperature for 2 h. The mixture was quenched with water (100 ml). The organic layer was separated. The aqueous layer was extracted with dichloromethane (100 ml×3). The combined organic layer was washed with brine (50 ml), dried (MgSO4), and concentrated. Purification by flash column chromatography eluting with hexane/ethyl acetate (gradient elution from 2:1 to 1:1) to afford 1.51 g (98%) of the title compound as an orange solid.

Workup

  1. customThe mixture was quenched with water (100 ml)
  2. customThe organic layer was separated
  3. extractionThe aqueous layer was extracted with dichloromethane (100 ml×3)
  4. washThe combined organic layer was washed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by flash column chromatography
  8. washeluting with hexane/ethyl acetate (gradient elution from 2:1 to 1:1)

Sources & evidence

ORD record
ord-90bdaad0f5124f70b22c45fcf6580acb
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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