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

HRID 2077744Notes

Reaction equation

HRID 2077744 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-561c7b94a92e409e91cdc417075a1954
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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